Tentative Rules for Carbohydrate Nomenclature · Tentative Rules for Carbohydrate Nomenclature Part 1, 1969 ... aspects of the nomenclature of carbohydrates ... the carbonyl group

‘Ikz JOWRNAL OF R~LO~ICAL CHEMI~TRV Vol. 217, No. 3, Issue of Fchruary 10, pp. 613-635, 1972

Printed in U.S.A.

Rule

Cub-1 Carb-2 Garb-3 Carb-4 Garb-5 Carb-6 Garb-7 Garb-8 Carb-9 Carb-10 Garb-11 Garb-12 Carb-13 Garb-14

Garb-15 Garb-16 Garb-17 Garb-18

IUPAC Commission on the Nomenclature of Organic Chemistry (CNOC) and IUPAC-IUB Commission on Biochemical Nomenclature (CBN)

Tentative Rules for Carbohydrate Nomenclature

Part 1, 1969 *

CONTENTS

Page

Preamble .............. 613 Basis of the nomenclature ....... 614 Choice of parent structure ....... 615 Trivial and systematic names. ..... 615 Aldoses and ketoses .......... 615 Trivial names. ............ 615 Stem names ............. 615 Configurational symbols ........ 615 Configurational prefixes ........ 615 Multiple configurational prefixes .... 616 Monoketoses ............. 617 Diketoses .............. 617 Aldoketoses 618 Dialdoses . : : .... : : .............. 618 Deoxy-monosaccharides and amino-monosaccharides. ............. 618 O-Substitution ............ 620 O-Substitution ............ 629 Acyclic forms. ............ 620

20 Ring size in cyclic forms ........ 621

In 1964 the Commission on the Nomenclature of Organic Chemistry of the International Union of Pure and Applied Chemistry (IUPAC) formed a Special Committee on Carbo- hydrate Nomenclature’ to consider the existing Anglo- American Rules of Carbohydrate Nomenclature and to prepare a set of IUPAC Rules for Carbohydrate Nomen- clature. These Rules are now issued jointly by the IUPAC

* These Rules have been approved by the IUPAC Com- mission on the Nomenclature of Organic Chemistry (CNOC) and by the IUPAC-IUB Commission on Biochemical Nomen- clature (CBN) and are published by permission of IUPAC and IUB.

The Commissions will welcome comments and criticisms on and the notification of errors in this text of Tentative Rules for Carbohydrate Nomenclature; these should be sent to the chairman or secretary of either commission.

Commission on the Nomenclature of Organic Chemistry (Chairman: Prof. P. E. Verkade, Ary Schefferstraat 217, s’Gravenhage, The Netherlands; Secretary: Mr. S. P. Kles- ney, Central Report Index, 566 Building, Dow Chemical Co., Midland, Michigan 48640, U.S.A.), or to the:

Commission on Biochemical Nomenclature (Chairman : Prof. 0. Hoffmann-Ostenhof, Lehrkanzel fur Biochemie der Universitat, WahringerstraSe 38, A-1090 Wien, Austria; Secretary: Dr. W. E. Cohn, Biology Division, Oak Ridge National Laboratorv. P.O. Box Y. Oak Ridge. Tennessee

” ’ ” ,

37830, U.S.A.). 1 Comaosition: P. E. Verkade (chairman), J. E. Courtois,

I,. C. Crosi, 0. Hoffmann-Ostenhof, W. Kiyne, K. L. Loe- ning, N. Lozac’h, F. Micheel, T. Reichstein, J. Stanek, W. J. Whelan and M. L. Wolfram.

30 Eur. J. Biochem., Vol. 21

Rule

Garb-21 Garb-22 Garb-23 Garb-24 Garb-25 Garb-26 Garb-27 Garb-28 Garb-29 Carb-30 Garb-31 Garb-32 Garb-33 Garb-34 Garb-35 Carb-36 Garb-37 Garb-38 Garb-39 Garb-40

Anomers;useofcuandp. ..... o( and p not applicable. ...... Glycosides ............ Glycosyl radicals and glycosylamines Glycosyloxy radicals Alditols .. .... : 1 : : : : 1 o-Deoxyalditols ......... Aldonic acids. .......... Ketoaldonic acids ......... Uranic acids ........... Aldaric acids ........... Cyclic acetals. .......... Ortho esters ........... Acetals and thioacetals ...... Hemiacetals, etc. ......... Other sulfur monosaccharides. ... Intramolecular anhydrides ..... Intermolecular anhydrides ..... Disaccharides. .......... Tri- and oligosaccharides .....

Page

. 621

. 622 622 623

. 624 . 624 . 625 . 625 . 626

627 628

. 629

. 630

. 630 631

. 631

. 632 632

. 633 633

Commission on the Nomenclature of Organic Chemistry2 and the IUPAC-IUB Commission on Biochemical Nomen- clature3.

PREAMBLE

SCOPE OB TEE RULES

These Rules deal with the acyclic and cyclic forms of monosaccharides and their simple derivatives; oligosaccharides are also dealt with briefly.

Carbohydrate chemistry continues to provide a very fruitful field of research, such that it will be necessary, in the near future, to promulgate further Rules to cover the needs of developing areas, e.g. branched-chain and unsaturated monosaccharides, other carbohydrate acyclic and heterocyclic derivatives, conformational problems, polysaccharides.

USE OF THE RULES

These Rules are additional to the Definitive Rules for the Nomenclature of Organic Chemistry [l] and are intended to ~~ ___

2 Composition: P. E. Verkade (chairman), L. C. Cross, G. M. Dyson, K. L. Loening, N. Lozac’h, J. Rigaudy, S. P. Klesney and S. Veibel. Associate members: R. S. Cahn and H. Griinewald. Observers: K. A. Jensen and W. Klyne.

3 Present composition: 0. Hoffmann-Ostenhof (chairman), A. E. Braunstein, W. E. Cohn (secretary), P. Karlson, B. Keil, W. Klyne, C. Liebecq, E. C. Slater, E. C. Webb and W. J. Whelan. Observers: R. Dybkaer, K. L. Loening and S. Veibel. J. S. Fruton was a member of the Commission dur- ing the preparation of this document.

613

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614 IUPRC-IUB Tentative Rules for Carboh~Jd~ate Nomenclature

govern t.hose aspects of the nomenclature of carbohydrates not covered by those rules.

I. The Structure Named

These Rules are designed to name first a parent monosaccharide represented in the Fischer projection of the acyclic form and then its cyclic forms and derivatives.

The numbering system used in monosaccharides is based on the location of the (potential) carbonyl group. Modification of that group or introduction of further similar groups can therefore often destroy the uniqueness of the numbering system and permit a derivative to be named from more than one parent. In order to determine the unique systematic name of a derivative it is important to follow the procedure of establishing the Fischer projection of the appropriate parent monosaccharide, naming that according to the Rules, and thereafter deriving the name of any derivative.

2. Conventional Representations

a) The Fischer Projection. In this representation of a monosaccharide the carbon chain is written vertically with carbon atom number 1 at the top. The groups projecting to left and right of the carbon chain are considered as being in front of the plane of the paper. The optical antipode with the hydroxyl group at the highest-numbered asymmetric carbon atom on the right is then regarded as belonging to the n-series. It is now know that this convention represents the absolute configuration.

b) The Haworth Representation. The Haworth representation of the cyclic forms of monosaccharides can be derived from the Pischer projection, as follows. The monosaccharide is depicted with the carbon-chain horizontal and in the plane of the paper, the potential carbonyl group being to the right. The oxygen bridge is then depicted as being formed behing the plane of the paper.

The heterocyclic ring is therefore located in a plane approximately perpendicular to the plane of the paper and the groups attached to the carbon atoms of that ring are above and below the ring. The carbon atoms of the ring are not shown.

Groups that appear to the right of the vertical chain in the Fischer projection (A, D, below) then appear below the plane of the ring in the Haworth representation (B, C, E below). However, at the asymmetric carbon atom (C-5 in A; C-4 in D) involved via oxygen in ring formation with the carbon atom of the carbonyl group a formal double inversion must be envisaged to obtain the correct Haworth representation.

In the pyranose forms of n-aldohexoses C-6 will always be above the plane. In the furanose forms of n-aldohexoses the position of C-6 will depend on the configuration at C-4; it will, for example, be above the plane in n-glucofuranoses (e.g. C) but below the plane in n-galactofuranoses (e.g. E).

Examples :

Hg @; H”hH

b H,OH

(4 W (C)

a-n-Glucopyranose n-n-Glucofuranose (Fischer) (Haworth) (Haworth)

0% (E)

oc-n-Galactofuranose (Fischer) (Haworth)

Vol. 247, No. 3

CH,OH

Ho/R/ HWH

H OH

(F)

n-n-Galactopyranose (Haworth)

3. The Reference Carbon Atom and the Anomeric Prefix

a) The Reference Carbon Atom. This is defined as the highest-numbered asymmetric carbon atom in the monosaccharide chain.

b) The Anomeric Prejix. In a definitive name, the anomeric prefix (m or B) relates the configuration at the anomeric (or glycosidic) center to that of the reference carbon atom.

The anomer having the same orientation, in the Fischer projection, at the anomeric carbon atom and at the reference carbon atom is designated LY; the anomer having opposite orientations, in the Fischer project,ion, is designated B.

The anomeric prefix (a or ,O) can only be used in conjunc- tion with, and having the above-defined relation to, the configurational prefix (n or L) denoting the configuration at the reference carbon atom. Further, it may be used only when the locant of the anomeric center is smaller than that of the reference carbon atom.

4. Numbering of Monosaccharides

The basic principle for the numbering of monosaccharides gives the (potential) carbonyl group the lower of the possible numbers (cf. Rule Carb-4). This numbering system is usually retained even when a modification introduces a group which, on the basis of general organic chemical nomenclature, would have priority over the (potential) carbonyl group [e.g. in uranic acids the (potential) carbonyl group retains locant 1, despite the normal priority of the carboxyl group].

In ketoaldonic acids, the carboxyl group that replaces the original (formal) aldehyde group retains the locant 1.

5. New Asymmetric Centers

Not infrequently, derivatives of monosaccharides contain asymmetric carbon atoms not present in the parent monosaccharide. Examples include benzylidene derivatives, cer- tain other acetals, ortho ester structures, etc. When the stereochemistry at such a carbon atom is known it will be indicated in the name by use of the appropriat,e Sequence Rule symbol, R or S [2].

BASIS OF NOMENCLATURE

Rule Carb-1

The basis for the naming and numbering of a monosaccharide or monosaccharide derivative is the structure of the parent monosaccharide (CnHsnOn), represented in the Fischer projection of the acyclic form.


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Issue of February 10, 1972 CNOC uncz CRN 615

CHOICE OF PARENT STRUCTURE

Rule Garb-2

If, in naming a derivative, a choice of parent monosaccharide is possible, the selection of parent is made according to the following order of preference, treated in the order given until a decision is reached:

a) The monosaccharide, of which the first letter of the trivial name (Rule Garb-5), or of the configurational prefix, or of the first cited configurational prefix of a systematic name (Rule Carb-S), occurs earliest in the alphabet. If two possible parents have the same initial letter, then the choice will be made according to the letter at the first point of difference in the trivial name, the configurational prefix of the systematic name, etc. Examples: allose before glucose, glucose before gulose, allo- before gluco-, gluco- before gulo-.

b) The configurational symbol D- before L-.

c) The monosaccharide which gives the point(s) of modi-

fication of the )CH(OH) chain the lowest locant(s)4.

d) The monosaccharide which gives the lowest locants to the substituents, present in the derivative.

e) The monosaccharide which, when the substituents have been placed in alphabetical order, results in the first-cited substituent having the lowest locant4.

TRIVIAL AND SYSTEMATIC NAMES

Rule Curb-3

In naming monosaccharides or monosaccharide derivatives, either trivial or systematic names can be used for the parent monosaccharide.

Trivial names are defined in Rule Carb-5. Systematic names are formed by adding one or more

configurational prefixes (Rule Carb-8) to the appropriate stem name (Rule Carb-6).

Rule Curb-4

The names ‘aldose’ and ‘ketose’ are used in a generic sense to denote monosaccharides in which the (potential) carbonyl group is terminal (aldehydic) or non-terminal (ketonic), respectively. In an aldose, the carbon atom of the (potential) carbonyl group is atom number one; in a ketose it has the lower number possible.

Rule Curb-5

The trivial names of the acyclic aldoses with three, four, five, or six carbon atoms are retained, and are used in preference to their systematic names for the aldoses and for the formation of names of their derivatives. The trivial names of these aldoses are:

Triose : Tetroses: Pentoses : Hexoses :

glyceraldehyde (glycerose is not recommended) erythrose, threose arabinose, lyxose, ribose, xylose alloso, altrose, galactose, glucose, gulose, idose, mannose, talose.

Rule Curb-6

The ‘stem names’ of the acyclic aldoses having three, four, five, six, seven, eight, nine, ten etc., carbon atoms in the chain are triose, tetrose, pentose, hexose, heptose, octose, nonose, decose etc.

4 Lowest locants are defined as follows: when a series of locants containing the same number of terms are compared term by term that series is ‘lowest’ which contains the lowest number on the occasion of the first difference (see IUPAC Nomenclature of Organic Chemistry, Section C, 1965, p. 23, footnote).

The ‘stem names’ of the acyclic ketoses having four, five, six, seven, eight, nine, ten, etc., carbon atoms in the chain are tetrulose, pentulose, hexulose, heptulose, octulose, nonulose, deculose. etc.

CONFIGURATIONAL SYMBOLS AND PREFIXES

Rule Curb-7

Configurational relationships are denoted by the symbols D and L which in print will be small capital roman letters and which are not abbreviations for ‘dextro’ and ‘laevo’. Racemic forms may be indicated by DL. Such symbols are affixed by a hyphen immediately before the monosaccharide trivial name (Rule Garb-5) or before each configurational prefix (Rule Carb-8) of a systematic name, and are employed only with compounds that have been related definitely to the reference standard glyceraldehyde (see Rule Carb-8). The configurational symbol should not be omitted, if known.

If the sign of the optical rotation under specified condi- tions is to be indicated, this is done by adding (+) or (-). Racemic forms may be indicated by (+). With compounds optically compensated intramolecularly the prefix ‘meso' is used where appropriate.

Examples : D-Glucose or D(+)-glucose, D-fructose or D(-)-fructose, nn-glucose or (&)-glucose.

Rule Curb-8

The configuration of a

three or four contiguous

(:,,OH group or a set of two,

,,CHOH groups (or wholly or

partly derivative groups, such as )CHOCH 37) CHOCOCH,,

or > CHNH,) is designated by the appropriate one of the

following configurational prefixes, which are (except for glycero-) derived from the trivial names of the aldoses men- tioned in Rule Carb-5. When used in systematic names these prefixes are to be uncapitalized and are italicized in print. They are affixed by a hyphen to the stem name defined in Rule Garb-6. There may be more than one configurational prefix in a name.

Each prefix is D or L according to whether the configuration at the reference carbon atom in the Fischer projection is the same as, or the opposite of, that in D( +)-glyceraldehyde.

Only the Fischer projections of the D-prefixes are given below; X is the group with the lowest-numbered carbon atom(s).

One >

CHOH group:

X

H&OH

I Y

D-&/CWO-

Two >

CHOH groups:

x I

HCOH

I HCOH

I Y

D-erythro-

X

I HOCH

I HCOH

ir wthreo-


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616 I UPAC-I UB Tentative Rules for Carbohydrate Nomenclature Vol. 247, No. 3

Three

x

)CHOH gy:

I HOCH CI HO H

I HCOH HOCK

I HCOH

I Y

D-arabino- n-lyxo-

Four >

CHOH groups:

X.

I HCOH

I HCOH

I HCOH

I HCOH

!r D-allo-

X

I HCOH

I HCOH

I HOCH

I HCOH

I Y

D-&O-

X I

HOCH I

HCOH I

HCOH

c1 H OH

4 D-U&O-

X

b HO H

HCOH I

HOCH I

HCOH

4 D-idO-

X

I HCOH

b H OH

HCOH I

Y D-ribo-

X

I HCOH

HCOH

D-gal&o-

HOCH I

HCOH

I HCOH

D-manno-

X I

HCOH

c! HO H

f! H OH

4 D-X$0-

X I

HCOH I

HOCH

b H OH

HCOH

4 D-&CO-

X

I HOCH

c! HO H

HOCH I

HCOH I

Y D-ta10-

The systematic name for a monosaccharide is then formed by using the configurational symbols and prefixes with the appropriate stem name (Rule Garb-6).

For sets of more than four contiguous >

CHOH groups

see Rule Garb-9. The trivial names, which are preferred, of the acyclic

aldoses with four to six carbon atoms (Rule Garb-5) thus correspond to the following systematic names.

Trivial Systematic

D-Erythrose D-Threose D-Arabinose D-Lyxose D-Ribose D-Xylose D-Allose D-Altrose D-Calactose D-Glucose D-&dose D-Idose D-Mannose D-Talose

D-erythro-tetrose D-threo-tetrose D-arabino-pentose D-lyxo-pentose D-ribo-pentose D-xylo-pentose D-allo-hexose D-a&o-hexose D-galacto-hexose D-glue&hexose D-gulo-hexose D-ido-hexose D-manw-hexose D-tale-hexose

Note: Anglo-American Usage

Since 1952, usage in the United States and the United Kingdom has been based on a different significance for configurational prefixes in that they have been related to a sequence of consecutive but not necessarily contiguous asymmetric groups.

Examples:

X

c! HO H

Ii

c! H OH

X X

I HOCH

I HCOH 4

74 HCOH

I I HCOH HCOH i!

4 ? HCOH I

Y all D-arabino

N and M are each a single non-asymmetric carbon center or a sequence of non-asymmetric carbon centers.

Ketoses and Deoxysaccharides. Prefixes with this significance were used when N is the methylene group of a deoxy compound or the keto group of a ketose containing not more than four asymmetric carbon centers, but not the keto group of a higher-sugar ketose.

Examples: Names according to this usage are given in notes to the subsequent Rules.

MULTIPLE CONFIGURATIONAL PREFIXES

Rule Curb-9

An acyclic monosaccharide containing more than four contiguous asymmetric carbon atoms is named by adding two or more prefixes, together indicating the configurations at all the asymmetric carbon atoms, to the stem name defined in Rule Garb-6.

The configurational prefixes employed are given in Rule Carb-8. The sequence of (4n + m; where n is 1 or more and m is 0, 1,2, or 3) asymmetric carbon atoms is divided, beginning at the asymmetric carbon atom next to the functional group, into (n) sets of four asymmetric carbon atoms, and a final set (m) of less than four. The order of citation of these prefixes commences at the end farthest from carbon number one.

The locants corresponding to the configurational prefixes may be inserted in the name, if desired. In such cases, all locants are given and immediately precede the appropriate configurational prefixes.

Examples : HC=O

b H OH

HOCH

I HCOH

I HCOH

H&OH I

CH,OH D-glycero-D-gluco-Heptose

or 6-D-glycero-2,3,4,5-D-gluco-Heptose


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Issue of February 10, 1972 CNOC and CRN

HC=O CH,OH I

HObH

Lo I

HCOH I

HCOH I

HObH \

I HOCH

I HOCH

I / CH,OH

L-ribo-n-manno-Nonose or 6,7,8-n-ribo-2,3,4,5-o-manno-Nonose

Comment. Compounds that require multiple configurational prefixes but which do not necessarily contain more than four contiguous asymmetric carbon atoms are covered by Rules (Lb-10 (ketoses) and Carb-14 (deoxysaccharides).

KETOSES

Rule Garb-10

Ketoses are classified as 2-ketoses, 3-ketoses, etc., according to the position of the (potential) carbonyl group (see Rule Garb-4).

The systematic name of an individual ketose is obtained by affixing, before the stem name (Rule Garb-6) and by means of a hyphen, the locant of the (potential) carbonyl group. The locant is preceded by the configurational prefix or prefixes (Rule Carb-8) for the groups of asymmetric centers present.

If more than one configurational prefix is needed, the order of their citation commences at the end farthest from carbon atom number one.

The locant 2 may be omitted from the name of a 2-ketose when no ambiguity can arise5.

When the carbonyl group is at the middle carbon atom of a ketose containing an uneven number of carbon atoms in the chain two names are possible. That name will be selected as accords with the order of precedence given in Rule Carb-2.

Examples:

CH,OH I

CH,OH

c=o I c=o

I HCOH

I HCOH

C&OH I

HCOH I

CH,OH

n-glycero-2-Tetrulose n-erythro-2-Pentulose

5 In this text, the locant is always retained for the sake of clarity.

~H,OH

D-erythro-L-glycero- 3-Hexulose a

617

CH,OH I c=o I

HOCH I

HCOH

I HOCH

I HOCH

I CH,OH

L-gluco-2-Heptulose

CH,OH I

HCOH

Lo

L-glycero-rballo- n-glycero-3-Nonulose

CH,OH I

HOCH I

j HCOH I

HOCH

I c=o I

HOCH ’

HO&H

I HOCH

~H,OH

L-ribo-L-xylo&Nonulose not n-xylo-n-ribo-5-Nonulose

[see Rule Garb-2(a)]

The following are examples of non-systematic names of ketoses that are established by usage and may be retained.

o-Ribulose for D-XyldOSe for Sedoheptulose for

D-Fructose for o-Psicose for n-Sorbose for D-Tagatose for

o-erythro-2-pentulose n-three-2-pentulose n-altro-2-heptulose

n-arabino-2.hexulose n-ribo-2-hexulose n-xylo-2-hexulose n-lyxo-2-hexulose

Rule Carb-11 DIKETOSES

Monosaccharide derivatives containing two (potential) ketonic carbonyl groups have the general name diketose.

The systematic name of an individual diketose is derived by use of the termination ‘odiulose’ in place of the termination ‘ulose’ characteristic of the monoketose (Rule Carb-6). The locants of the (potential)carbonyl groups are the lowest possible numbers (see Rule Carb-4) and are inserted together with a hyphen before the stem name. They are in turn preceded by configurational prefixes, the latter as prescribed in Rules Garb-8 and Garb-9. The order of citation of these prefixes commences at the end farthest from carbon atom number one.

Note. It sometimes happens that, when the carbonyl groups are symmetrically placed along the carbon chain, two systematic names are possible; that name is selected as accords with the order of precedence given in Rule Carb-2.

a Name according to Anglo-American usage: n-arabino- Y-hexulose.


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618 I UPAC-I UR Tentative Rules for Carbohydrate Nomenclature Vol. 247, No. 3

Examples :

CH,OH I c=o I c=o I

HCOH

I CH,OH

n-glycero-2,3-Pentodiulose

CH,OH

I c=o I

HOCH

I c=o I

HCOH

I CH,OH

u-glycero-L-glycero- 2,4-Hexodiulose7 ca)

(not u-glycero-L-glycero- 3,5-Hexodiulose)

[See Rule Garb-B(b)]

CH,OH I c=o I

HCOH I

HOCH

b-0

I CH,OH

L-three-2,5-Hexodiulose

CH,OH I

HCOH I

HOCH I c=o I c=o I

HOCH I

HOCH I

CH,OH L-erythro-L-threo- 4,5-0ctodiulose7(b)

(not L-threo-werythro- 4,5-Octodiulose)

[See Rule Garb-2(a)]

Rule Garb-12 ALDOKETOSES

Monosaccharide derivatives containing a (potential) aldehydic carbonyl group and a (potential) ketonic carbonyl group have the general name aldoketose.

Names of individual aldoketoses are formed in the same way as those of diketoses. but by the use of the termination ‘osulose’ in place of the termination ‘ose’ of the corresponding aldose (Rule Carb-6). The carbon atom of the (potential) aldehydic carbonyl group is numbered one, and this locant is not cited in the name. The locant of the (potential) ketonic carbonyl group is given unless it is 2 ; it may then be omitteds.

Examples :

HC=O I c=o I

HCOH I

HCOH

I CH,OH

HC=O I

HOCH

LO

I HCOH

I HCOH

I:H,~H

D-erythro- 2-Pentosulose

u-erythro-L-glycero- 3-Hexosulose9

7 Names according to Anglo-American usage: (a) D-threo- 2,4-hexodiulose, (b) L-altro-4,5-octodiulose.

s In this text, the locant is always retained for the sake of clarity.

9 Name according to Anglo-American usage: D-arabino- 3-hexosulose.

HC=O I c=o I

HOCH I

HCOH

I HOCH

I HOCH

~H,OH L-gluco-2.Heptosulose

Comment: 2-aldoketoses have also been named as ‘osones’ but this practice is not recommended.

Rule Carb-13 DIALDOSES

Monosaccharide derivatives containing two (potential) aldehydic carbonyl groups have the general name ‘dial- dose’. Names of individual dialdoses are formed in the same way as those of diketoses, but by the use of the termination ‘odialdose’ in place of the termination ‘odiulose’. Locants are not needed.

Examples :

HC=O

I HCOH

I HOCH

I HC=O

HC=O I

HCOH I

HOCH I

HOCH

L-threo- Tetrodialdose

HAOH

I HC=O

meso-qalacto- Hexodialdoselo

HC=O

I HCOH

I HOCH

I HCOH

I HCOH

I HC=O

I,-g&o-Hexodialdose not L-gulo-Hexodialdose

DEOXY-MONOSACCHARIDES AND AMlNO-MONOSACCHARIDES

Rule Garb-14

a) The replacement of an alcoholic hydroxyl group of a monosaccharide, or monosaccharide derivative, by a hydrogen atom is expressed by using the prefix ‘deoxy’, preceded by the appropriate locant and followed by a hyphen together with a systematic or trivial name (Rule Carb-3). The systematic name consists of a stem name with such configurational prefixes as express the configurations at t,he

lo The prefix meso- may precede the name of such sym- metrical compounds, for the sake of clarity.


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Issue of February 10, 1972 CNOC and CBA- 619

asymmetric centers present in the deoxy-compound. The order of citation of the configurational prefixes commences at the end farthest from carbon atom number one.

A trivial name may be used only if the transformation of the saccharide into the deoxy-compound does not alter the configuration at any asymmetric center.

Examples:

HC-0 I

HCOH I

CH,

CH,OH I

c=o I

HCOH

HCOH I

HCOH I CH,OH

3.Deoxy-n-erythro- n-glycero-hexose’i

I CH,

CH,OH

&Deoxy-n-glycero- 2-pcntulose

HC=O HC=O I I

CH, HCOH

I I HOCH HCOH

I I HCOH HOCH

I I HOCH IICOH

I I CH,OH CH,

%-Deoxy-L-rylo-hexose 6.Deoxy-D-gulose

Trivial names of 6-deoxy-hexoses established by usage may be retained and used for the formation of names of derivatives.

Examples:

HC=O I

HCOH I

HOCH I

HOCH I

HCOH

HC=O I

HCOH I

HCOH I

HOCH I

HOCH I CH,

I CH,

D-Fucose

(6.Deoxy-n-galactose) L-Rhamnose

(6.Deoxy-L-mannose)

The following is established as a trivial name for biochemical use: deoxyribose for 2-deoxy-n-erythro-pentose.

b) The replacement of an alcoholic hydroxyl group of a monosaccharide, or monosaccharide derivative, by an amino group is envisaged as substitution of the appropriate hydrogen atom of the corresponding deoxy-monosaccharide by the amino group.

Substitution in the amino group is indicated by use of the prefix N (Rule Carb-15) unless the substituted amino group has a trivial name (for example: CH,CONH-, acetamido). .~~ ~~

Trivial names accepted for biochemical usage : u-Calactosamine for 2.amino-2.deoxy-n-galactopyranose

(the name chondrosamine is not recommended) n-Clucosamine for 2.amino-2-deoxy-n-glucopyranose n-JIannosamine for 2-amino-2-deoxy-n-msnnopyranose Seuraminic acid for 5-amino-3,s.dideoxy-ix-D-glycero-n-

gnlacto-2-nonulopyranosonic acid Muramic acid for 2-amino-3-0-[1-(8).carboxyethylj-2-deoxy-

a1dehydo.o.glucose When the complete name of the derivative includes

other prefixes, ‘deoxy’ takes its place in the alphabetical orderi of detachable prefixes; in citation the alphabetical order is preferred to numerical order.

I1 Name according to Anglo-American usage: 3-deoxy- l2 See IUPAC Nomenclature of Organic Chemistry, n-riho-hexose. Section C, 1965, Rules C-16.1 and C-16.4,

The stereochemistry at the carbon atom carrying the amino group is expressed according to Rule Carb-8.

I HCN II,

I HOCH

CH,OH

2-Amino-2-deoxy- cr-n-glucopyranose

HCOH

HANH-COCH, I

HOCH

c H ‘OH

c1 HO

CH,OH

2Acetamido-2.deoxy- a-D-glUCOpyranOSe

c! H OH

HCOH I

CH,OH

(4

(A) 5-Amino-3,5-dideoxy-cx-D-glycero-u-galacto-2-nonulopyranosonic acid

CHO

HCNH, I

I HC-COOH

I HCOH

I CH,

I HCOH

I CH,OH

(W

(IX) 2-Amino-3-O-[l-(S)-carboxyethyl]-2-deoxy-~Z~e~y~o- u-glucose


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Examples: HC=O HC=O 4-Amino-4-deoxy-3.O-methyl-D-erythro-2-pentalose I I 4-Deoxy-4-(ethylamino)-D-erythro-2-pentulosc HCOH HCOH

I I O-SUBSTITUTION HCOH HOCH

Rule Cat-b-15 I I Replacement of the hydrogen atom of an alcoholic hydro-

HOCH HCOH

xyl group of a saccharide or saccharide derivative by another I I atom or group is denoted by placing the name of this atom

HOCH HCOH

or group before the name of the parent compound. The name I I of the atom or group is preceded by an italic capital letter 0

CH,OSO,C,H,CH,-p CH,OPO&

(for oxygen), followed by a hyphen in order to make clear r,-Kannose 6-p-toluenesulfonate o-Glucose 6-(di-

that substitution is on oxygen. The 0 prefix need not be re- not 6.tosylate; potassium phosphate)

peated for multiple replacements by the same atom or group. (see Rule C-641.5, examples) (permitted biochemical

Replacement of hydrogen attached to nitrogen or sulfur usage: glucose

by another atom or group is indicated in a similar way with B-phosphate)

the use of italic capital letters N or S (for examples see Rules Carb-24 and Carb-36). ACYCLIC FORMS

The italic capital letter C may be used to indicate replace- Rzcle Garb-17 ment of hydrogen attached to carbon, to avoid possible ambiguityr2. The acyclic nature of a monosaccharide or monosac-

charide derivative containing an uncyclised carbonyl group Examples: may be stressed by inserting the italicized prefix ‘nldehydo’

HC=O HC=O HC=O or ‘keto’ respectively, immediately before the configurational

I I HbOCOCH,

prefix(es) or before the trivial name. These prefixes may be

HOCH HOCCH, abbreviated to ‘al’ and ‘ke’.

I I I HCOH HCOC,H, HOCH

I I HCOH HLOCOCH,

Examples :

C,H,OCH HC=O

I I I I HCOH CH,OH HCOH HCOCOCH,

I I I

CH,OH CH,OH CH,COObH

4-O-Ethyl- 3-O-Ethyl-2- 2,4-Di-O-acetyl- I D-idose C-methyl- D-glucose

HCOCOCH,

D-arabinose I

HCOCOCH,

HC=O I

I CH,OCOCH,

HCOH 2 3 4 5 6-Penta-O-acetyl-alehydo-D-glucose , f , t

I aldehydo-D-Glucose 2,3,4,5,6-pentaacetate

HCOH I

HOCH CH,OCOCH,

I I co

HOCH

CH,OSO,C,H,CH,-P 6.0-Tosyl-L-mannose

Rule Garb-16 (Alternative to Rule Carb-15) O-Substitution products of saccharides or saccharide

derivatives may be named as esters, ethers, etc., following the procedures prescribed for that purpose in IUPAC Nomen- clature of Organic Chemistry, Section C, 1965.

Examples : HC=O HC=O HC=O

I I HCOH HCOH HAOCOC,H,

I I I CH,OCH CH,COOCH HCOH

I I I HCOH HCOH HOCH

I I I HCOH HCOH HCOH

I I CH,OH CH,OH CIH,

D-Glucose D-Glucose 6-Deoxy-D-gulose S-methyl ether &acetate

. Z- benzoate

CH,COO(!H I

H(i:OCOCH,

HbOCOCH, I

CH,OCOCH, 1,3,4,5,6-Penta-O-acetyl-keto-D-fructose keto-D-Fructose 1,3,4,5,6-pentaacetatc

HC=O I

HCOCH, I

04: \ a HbOCH

AH, a

3,6-Anhydro-2,4,5-tri-O-methyl-aldehydo- D-galactose

620 IUPAC-ICJB Tentative Rules for Carbohydrate Nomenclature Vol. 247, No. 3


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CH,OH I

H,COCH I c=o I

HCOCH, I

HkOCH,

&H,OCH,

2,4,5,6-Tetra-O-methyl-keto-D-erythro- L-glycero-3.hexuloser3

Examples:

HCF I

HCOH I

HOCH I

HCOH I

HCOH

CH,OH I CH,O-

(a)i4 B-D-Galactopyranose (b) p-D-Galactose-(1,5)

oc-D-Glucoseptanose n-D-Glucose-(1,6)

RING SIZE IN CYCLIC FORMS

Rule Curb-18

The size of the ring in the cyclic form of a monosaccharide (aldose or ketose) or monosaccharide derivative may be indicated by replacing the terminal letters ‘se’ of the name of the acyclic form by ‘furanose’ for the 5-atom ring, ‘pyranose’ for the B-atom ring, and ‘septanose’ for the 7-atom ring.

Rule Curb-19 (Alternative to Rule Carb-18)

The size of the ring in the cyclic form of a monosaccharide (aldose or ketose) or monosaccharide derivative may be indicated by two numerals, placed in parentheses and joined to the end of the name of the acyclic compound by a hyphen. These numerals denote the two carbon atoms to which the ring oxygen atom is attached, the carbon atom of the potential carbonyl group being cited first.

Rule Curb-20

For cyclic forms of ketoses, diketoses, dialdoses, and aldoketoses, the names constructed according to Rule Carb-18 may, when necessary, be followed by a pair of numerals, these numerals having the same significance as in Rule Carb-19.

Comment. Examples of the application of Rules Carb-18- Carb-20 are given in Rules Carb-21 -Garb-23. The system of Rule Carb-18 is preferred, but that of Rule Carb-19 is ad- vantageous in special cases.

Rule Curb-21

ANOMERS

The free hydroxyl group belonging to the internal hemiacetal grouping of the cyclic form of a monosaccharide or monosaccharide derivative is termed the ‘anomeric’ or ‘glycosidic’ hydroxyl group.

The two cyclic forms of an aldose or ketose, or aldose or ketose derivative (termed anomers), are distinguished with the aid of the anomeric prefixes (L and b, relating the configuration at the anomeric carbon atom to that at the reference asymmetric carbon atom of the compound; the anomer having the same configuration, in the Fischer projection, at the anomeric and the reference carbon atom is designated CT.

The anomeric prefix, o( or /I, followed by a hyphen, is placed immediately in front of the configurational symbol, D or L, of the trivial name or of the configurational prefix denoting the group of asymmetric carbon atoms that includes the reference carbon atom (see Preamble, paragraph 3).

i3 Name according to Anglo-American usage: 2,4,5,6- tetra-O-methyl-keto-D-arabino-3-hexulose.

HOC-CH,OH I

HOCH I

HCOH

d H OH

AH,O-

(a)14 /?-D-Fructopyranose (b) p-D-Fructose-(2,6)

I HCOH

&H,~H

(a) 3-Deoxy-a-D-erythro-D-glycero-hexofuranoseij (b) 3-Deoxy-a-D-erythro-L-glycero-hexose-(1,4)

621

L’ HCOH

0 AH I

HCOH

~H,OH

(a) n-D-glycero-D-ido-Heptopyranose (b) oc-D-glycero-L-ido-Hepotse-(1,5)

I4 (a), (b) and (c), here and subsequently, refer to names coined in terms of Rules Garb-18, Carb-19, and Garb-20, respectively.

i5 Name according to Anglo-American usage: 3.deoxy- a-D-arabino-hexofuranose.


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Rule Garb-22

With ketoses that have the (potential) carbonyl group

located between two >

CHOH groups, each separated from

the carbonyl group by two, three, or four carbon atoms of the chain, ring-closure may take place towards either end of that chain. Likewise, with dialdoses, diketoses and aldoketoses ring-closure may take place from either (potential) carbonyl group towards the center of the chain.

In each case both cyclic forms have the same monosaccharide parent that dictates the basis of the name and numbering of each form (cf. Rule Carb-2). In one form the locant of the anomeric or glycosidic hydroxyl group is lower than that of the reference carbon atom ; t,hat cyclic form is named according to Rules Carb-18 and Carb-21. In the other the locant of the anomeric or glycosidic hydroxyl group must be higher than that of the reference carbon atom. This precludes (see Preamble, paragraph 3) the use of (Y and /3 to define the two anomers (Rule Garb-21), and the appropriate Sequence Rule symbol, R or S (see Preamble, paragraph 5), must be used, in place of o( or B, to indicate the configuration at the anomeric carbon atom.

Examples: CH,OH I

HCOH I

HOCH I

HOCH I

HOCH I

6 co

I HOCH

I HCOH

I

HOeH I

HOCH I

11 CH,OH L-gluco-L-altro-6.Undeculose, not L-tale-n-gulo-6-Undeculose

(cf. Rule Garb-2)

CH,OH I

HCOH

11 CH,OH

A H OH

H+OH

6 OH

HO bH I ss

HCOH I

HObH I

HOCH

dH bH

11 AH,OH

(b)14 (6S)-L-gluco-L-altro-6-Undeculose-(6,3) (c) (6S)-L-gluco-L-c&o-6-Undeculofuranose-(6,3)

CHO

I HCOH

I HOCH

I HCOH

I HCOH

I CHO

u-gluco-Hexodialdose, not L-g&o-hexodialdose (cf. Rules Carb-2 and Garb-11)

CHO

I HCOH

(c)l4 (BR)-n-gluco-Hexodialdopyranose-(6,2) (b) (GR)-n-gluco-Hexodialdose-(6,2)

Rule Curb-23 GLYCOSIDES

Mixed acetals, resulting from the replacement of the hydrogen atom of the anomeric or glycosidic hydroxyl group by a group X, derived from an alcohol or phenol (XOH), are named ‘glycosides’. The term ‘glycoside’ is used in a generic sense only, and may not be applied to specific compounds. Glycosides are named by replacing the terminal ‘e’ of the name of the corresponding cyclic form of the saccharide or saccharide derivative by ‘ide’ and placing before the word thus obtained, as a separate word, the name of the group X.

Examples:

I I

HCOH c OdH

H&OH I

CH,OH

(a) Methyl cx-n-gulofqranoside (b) Methyl ol-n-guloside-(1,4)

(a) Ethyl /?-n-fructopyranoside (b) Ethyl p-n-fructoside-(2,6)


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&HO (a) Methyl n-n-gluco-hexodialdopyranoside-(1,5) (b) Methyl n-n-g&o-hexodialdoside-(1,5)

CHO I

HCO.-3

I HOCH

I HCOH

I HCOH I

HhOCH, j

(a) Methyl (6R)-n-gluco-hexodialdopyranoside(6,Z) (b) Methyl (6R)-n-gluco-hexodialdoside-(6,2)

OH

HOCH, b

(a) Methyl a-D-gkco-D-glycero-3-octuloseptanoside (b) Methyl n-D-gluco-D-glycero-3-octuloside-(3,8)

GLYCOSYL RADICALS AND GLYCOSYLAMINES

Rule Garb-24 a) The radical formed by detaching the anomeric or

glycosidic hydroxyl group from the cyclic form of a monosaccharide or monosaccharide derivative is named by replacing the terminal ‘e’ of the name of the monosaccharide or monosaccharide derivative by ‘~1’. The general name of these radicals is ‘glycosyl’ (glycofuranosyl, glycopyranosyl, glycoseptanosyl) radical.

Examples:

HCr13r‘--7

CH,OkH

I HCOCH,

I HCOH I

H&O-

&OH

(a) 2,3-Di-O-methyl-a-n-altropranosyl bromide (b) 2,3-Di-O-methyl-x-n-altrosyl-(1,5) bromide

HCrOOC,H, I

HCOH I

HCOH

I HCOH

I HCO-

I CH,OH

(4 n-n-Allopyranosyi benzoate (or l-O-benzoyl-n-n-allopyranose)

(b) a-D-Allosyl-(1,5) benzoate [or l-o-benzoyl-n-D-allose-(1,S)1

c HCOPO,K,

I HCOH

b HO H

A H OH

HCO-

&H,~H

(a) n-n-Glucopyranosyl dipotassium phosphate (b) or-D-Glucosyl-(1.5) dipotassium phosphate

(common name for biochemical usage: oc-glucose l-phosphate)

HC-

I HCNHCOCH,

I HOCH

I HCOH

I HCO

I CH,OH

(a) 2-Acetamido-2-deoxy-or-u-glucopyranosyl isocyanate (b) 2Acetamido-2-deoxy-n-u-glucosyl-(15) isocyanate

b) The replacement of the glycosidic hydroxyl group of a cyclic form of a monosaccharide derivative by an amino group is indicated by adding the suffix ‘amine’ to the name of the glycosyl radical.

Example :

C,H,NHCc I

HOCH

I HCOH

I HCOH

I CH,O-

(a) N-Phenyl-,%n-fructopyranosylamine (b) N-Phenyl-b-wfructosyl-(2,6)-amine


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624 I UPAC-I UB Tentative

GLYCOSYLOXY RADICALS

Rule Garb-25

The radical formed by removal of the hydrogen atom from the anomeric or glycosidic hydroxy! group of the cyclic form of a monosaccharide or monosaccharide derivative is named by replacing the terminal ‘e’ of the name of the saccharide by ‘yloxy’.

Examples:

Rules for Carbohydrate Nomenclature Vol. 247, No. 3

HdlOCH,COOH I

HCOH I

HOCH

CH,OH

(a) cw-D-Glucopyranosy!oxyacetic acid (b) oc-D-G!ucosy!oxy-(1,5)-acetic acid

a-D-Arabinopyranosyloxyammonium chloride n-D-Arabinosyloxy-(1,5)-ammonium chloride

ALDITOLS

Rue Carb-26

a) Names for the polyhydric alcohols (alditols) of the saccharide series are derived from the names of the corresponding acyclic aldoses by changing the suffix ‘ose’ to ‘itol’.

If the same aldito! can be derived from two different aldoses preference is given to that name which accords with the order of precedence given in Rule Carb-2.

Examples :

CH,OH CH,OH

I I HCOH HOCH

I I HOCH HCOH

I I CH,OH HCOH

I CH,OH

HCOH

HOCH

HCOH

HOCH

HCOH

CH,OH 7

L( -)-Threitol D-Arabinitol meso-D-glycero-L-ido-Heptitol (not D-lyXitO1) (not L-glycero-D-ido-heptitol; cf. Rule Carb-2)

CH,OH I

HCOH I

HOCH I

HCOH I

HCOH

&H,OH

D-Glucito! (not L-gulitol)

Non-preferred trivial name: sorbito!

CH,OH

c: H OH

HOCH I

HOCH I

HOCH

~H,OH

L-Altritol (not L-talitol)

CH,OH CH,OH I

HOCH I

HOCH I

HCOH b HO H

I HCOH HCOH

I HOCH

I HOCH

I HCOH

I HCOH

I HCOH

I

~H,OH

CH,OH

D-erythro-L-galucto-Octito! D-glycero-L-gulo-Reptitol (not D-three-L-gulo-octitol) (not D-glycero-D-ido-heptito!)

Note. Names such as ‘mannite’ for mannitol are de- precated.

b) To the trivial names of alditols optically compensated intra molecularly, which have no D- or L- prefix, the prefix meso-may be added for the sake of clarity.

Examples : meso-erythritol, meso-ribito!, meso-xylito!, meso-allito!, meso-galactito!.

The prefixes D and L must however be used (i) in the names of meso-alditols containing more than four contiguous asymmetric carbon atoms in order to define the steric relation of the configurational prefixes cited and (ii) in naming derivatives of meso-alditols that have become asymmetric by substitution.

Examples :

0) CH,OH 1


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Issue of February 10, 1972 CNOC und CRN 625

(ii) CH,OH 1 I

HCOH I

HOCH

I HCOCH,

I CH,OH 5

4-O-Methyl-n-xyhtol (not 2-0-methyl-L-xylitol; cf. Rule Carb-2)

Rule Garb-ZY

o-DEOXYALDITOLS

and The name of an aldose derivative having a terminal CH, CH,OH group is derived from that of the appropriate

alditol (Rule Carb-2) by use of the prefix ‘deoxy’)

Examples:

CH, 1 I

HOCH

I HCOH

b H OH

CH,OH 5

CH,OH I

HOCH I

HOCH

HbOH

I CH,

l-Deoxy-o-arabinitol (not 5-deoxy-n-lyxitol)

CH,OH 1 I

CH,

HOCH HOCH I

HCOH I

HOCH I

HCOH I

HCOH I

CH, 5 ~H,OH 5Deoxy-n-arabinitol (not l-deoxy-w1yxitol)

CH, 1 I

CH,OH

HOCH CI HO H I

HCOH HOCH I

HCOH I

HOCH I

HCOH I

HCOH I

CH,OH 6 I CH,

1-Deoxy-n-altritol (not 6-deoxy-D-talitol)

Rule Garb-28 ALDONIC ACIDS

Monocarboxvlic acids formallv derived from aldoses. having three ok more carbon atoms in the chain, by oxidation of the aldehydic group, are named aldonic acids, and are divided into aldotrionic acid, aldotetronic acids, aldopentonic acids, aldohexonic acids, etc., according to the number of carbon atoms in the chain. The names of individual compounds of this type are formed by replacing the ending ‘ose’ of the systematic or trivial name of the aldose by ‘onic acid’.

Derivatives of these acids formed bv change in the carboxyl group (salts, esters, lactones, acyi halides, amides, nitriles, etc.,) are named according to the IUPAC Nomen- clature of Organic Chemistry, Section C, 1965, Rules C-4.

Examples:

COOCH, I

HCOCOCH, I

CH,COOCH

CHsCOOAH

b H,OCOCH,

Methyl tetra-o-acetyl- L-arabmonate or methyl

L-arabinonate tetraacetate (cf. Rule C-463)

COONa I

HCOH

I HOCH

I HCOH

I HCOH

dH,0~

Sodium D-&ICOnate

(cf. Rule C-461)

COOH I

HCNH, I

HOCH

I HCOH

I HCOH

I CH,OH

2-Amino-2-deoxy-n-gluconic acid (Common name for biochemical usage: n-Glucosaminic

acid)

c= I

HCOH I

HOCH I

HCOH

HCOH I

HCO- I

CH,OH I CH,OH

n-Glucono-1,4- lactone n-Glucono-1,5-la&one or, less preferred,

D-&lCOnO-y-hCtOUe

or, less preferred, D-glucono-8-lactone

(cf. Rules C-472.1 and C-472.4)

CN I

HCOCH,

CH,OdH

d CH,O H

HOCH

I CHsOCH,

2,3,4,6-Tetra-O-methyl-L-altrononitrile


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626 I UPAC-I UR Tentative Rules for Carbohydrate Nomenclature Vol. 247, No. 3

COOCH,

HOCH I CH,

HCOH

I CH,OH

Methyl 3-deoxy-n-glycero-L-glycero-pentonate’6 @)

I CH,OH

KETOALDONIC ACIDS

Rule Curb-29

Keto-carboxylic acids formally derived by oxidation of a secondary alcoholic hydroxyl group of an aldonic acid have the genera1 name ketoaldonic acids.

The carbon atom of the carboxyl group is numbered 1. Names of individual ketoaldonic acids, or of the glycosides

derived from such compounds, are formed by replacing the ending ‘ose’ or ‘oside’ of the appropriate ketose, or of the glycoside derived there from, by ‘osonic acid’ or ‘osidonic acid’ respectively.

Derivatives of these acids formed by modifying the carboxyl group (salts, esters, lactones, acyl halides, amides, nitriles, etc.) are named according to the IUPAC Nomencla- ture of Organic Chemistry, Section C, 1965, Rules C-4.

Examples:

COOH COOH

4 =o I

HCOH

c: H OH I

c=o

HCOH

c! H,OH

n-erythro-Z-Pentulosonic acid

&H,~H

D-glycero- 3-Tetrulosonic acid

is Names according to Anglo-American usage: (a) methyl 3-deoxy-n-three-pentonate, (b) 3.deoxy-n-ribo-hexono- 1,5-lactone.

COOH I

HOCH

I c=o I

HCOH

A H OH

AH,OH n-erythro-L-glycero-3-Hexulosonic acidi

n-n-arabino-2-Hexulopyranosonic acid (Common name for biochemical usage: 2.Keto-n-gluconic

acid)

p-n-arabino-2-Hexulopyranosono-1,5-lactone

Methyl a-n-or&no-2.hexulopyranosidonic acid

Methyl /3-n-arabino-2-hexulopyranosidonamide

i7 Name according to Anglo-American usage: n-arabino- 3-hexulosonic acid.


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Comnlent. Parentheses are suitably inserted where it is necessary to distinguish between an ester alkyl group and the hemiacetal alkyl group of a glycoside of a ketoaldonic acid.

C,H,OOC-?!OCH, I

HOCH I

HCOH 1

Ethyl (methyl a-u-arabino-2.hexulopymnosid)onate

-1 SaOOC--dOC,H,

I HOCH

I HCOH

I HCOH

I CH,O -

Sodium (ethyl n-n-arabino-2.hexulopyranosid)onate

URONIC ACIDS

Rule Garb-30

The monocarboxylic acids formally derived by oxidation of the terminal CH,OH group of aldoses having four or more carbon atoms in the chain, or of glycosides derived from these aldoses, to a carboxyl group are named ‘uranic acids’. The names of the individual compounds of this type are formed by replacing (a) the ‘ose’ of the systematic or trivial name of the aldose by ‘uranic’ acid or (b) the ‘oside’ of the name of the glycoside by ‘osiduronic acid’.

The carbon atom of the (potential) aldehydic carbonyl group (not that of the carboxyl group) is numbered 1.

Derivatives of these acids formed by change in the carboxyl group (salts, esters, lactones, acyl halides, amides, nitriles, etc.,) are named according to the IUPAC Nomen- clature of Organic Chemistry, Section C, 1965, Rules C-4.

Examples:

COOH

cx-n-Mannopyranuronic acid

&OOCH,

Methyl p-n-galactopyranuronate

HOCH I

COONa

Sodium a-L-glucofuranuronate

HCOCOC,H, I COOC,H,

Ethyl 2,3,5-tri-@benzoyl-m-n-mannofuranuronate

oc-n-Mannopyranurono-6,2-la&one

HCOPO,H,

HCOH

HOCH

J

HCOH

HCO

COOH

n-n-Clucopyranuronic acid l-(dihydrogen phosphate)


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82X IUPAC-IUB Tentative Rules for Carbohydrate Nomenclature Vol. 247, No. 3

Hi:OH

I CH, I

HOCH I

HO&H

I HCO-

H&OH I

COOH

2-Deoxy-n-n-manno-heptopyranuronic acid

HC=O

I CH,

HCOH I

HCOH

I CH, I

HCOH

&OOH

2,B-Dideoxy-aldehydo-D-glycero-D-erythro-heptllronic acidi*

I

HCOCH, I

CH,OCH

HO bH I

HCOH I

HCO-

I COOH

Methyl 2-O-methyl-a-n-mannopyranosiduronic acid

HCOCOC,H,

&OOH

Ethyl 2,3,5-tri-O-henzoyl-n-n-mnnnofuranosiduronic acid

H;OCH, I

CH,OCH I

HOCH

I HCOH

I HCO-

I COOC,H,

1

Ethyl (methyl 2.O-methyl-n-n-mannopyranosid)uronate

I HOCH

I HOCH

LOONa Sodium (methyl 3-deoxy-2-O-methyl-/I-L-manno-

L-glycero-octopyranosid)uronateig

Rule Garb-31

ALDARIC AClDS

The dicarboxylic acids formed by oxidation of both terminal groups of an aldose to carboxyl groups are called ‘aldaric acids’. Names of individual compounds of this type are formed by replacing the ending ‘ose’ of the systematic or trivial name of the corresponding aldose by ‘aric acid’. Choice between the several possible names is based on the order of precedence given in Rule Garb-2.

Examples :

a) Names requiring D or L:

COOH COOH COOH COOH I I

b H OH I

HCOH HOCH HCOH I I I

HOCH HCOH HOCH HOCH

b I I

HOCH I

OOH HCOH HCOH

c: OOH b HO H I

HCOH I

COOH COOH L-Threaric D-Arabinaric L-Altraric mGlucaric

acid acid acid acid (not (not (not

n-lyxaric L-talaric L-gularic acid) acid) acid)

r* Name according to Anglo-American usage: 2,5-dideoxy-aldehydo-n-ribo-hepturonic acid.

rs Name according to Anglo-American usage: sodium (methyl 3-deoxy-2-O-methyl-~-glycero-~-~-gaZacto-octopyranosid)uronate.


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Issue of February 10, 1972 CNOC and CBN

COOH COOH I

HCOH

b HO H

AOOH OOH

L-glycero-D-gala&o-Heptaric acid not L-glycero-n-g&o-Heptaric acid

b) To the names of aldaric acids optically compensated intramolecularly, which therefore have no D or L prefix, the prefix meso- may be added for the sake of clarity. Examples: meso-erythraric acid, meso-ribaric acid, meso-xylaric acid, meso-allaric acid, meso-galactaric acid.

The D or L prefix must however be used when a meso- aldaric acid has become asymmetric as a result of substitution.

c) The following trivial names are preferred to the systematic names.

COOH COOH COOH I

HCOH b HO H b H OH

b HO H A H OH b H OH

COOH dOOH COOH

(+)-Tartaric acid (-)-Tartaric acid meso-Tartaric acid (L-threaric acid) (u-threaric acid) (erythraric acid)

(RR-Tartaric acid) (SS-Tartaric acid) (RS-Tartaric acid)

CYCLIC ACETALS

Rule Curb-32

Cyclic acetals formed by the reaction of saccharides or saccharide derivatives with aldehydes or ketones are named in accordance with Rule Carb-15, bivalent radical names being used as prefixes, the names of such radicals following the rules of general organic chemical nomenclature. In indicating more than one cyclic acetal grouping of the same kind, the appropriate pairs of locants are separated typographically when the exact placement of the acetal groups is known.

Examples:

CH,OH I

HbO,

c! H,OH

2,4-O-Methylenexylitol

(CH ) Cd:!:

3 2 \OAH

1,3:4,6-Di-O-isopropylidene-n-mannitol

HdrO

c! ‘WH,),

H 0’

b H OH

HzOH

1,2-f%Isopropylidene-a-D-glucofuranose

AH,0 J

H AO’%H 3

1,2: 3,4-Di-0-set-butylidene-/?-D-arabinopyranose

C,H,\ ,OtiH

CHf C\O&H

HdO \ ,W,

/ HCOCH,

A H OH

A HO H

b X&- b CHC,H,

H20’

Methyl 4,6-O-benzylidene-a-n-glucopyranoside

I HCOH

&H,OH

1,2-O-(2-Chloroethylidene)~a-D-glucofuranose


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630 IUPAC-IUB Tentative Rules for Carbohydrate Nomenclature Vol. 247, No. 3

Note. It is to be noted that in the last three examples new asymmetric centers have been introduced at the carbonyl carbon atom of the aldehyde or ketone that has reacted with the saccharide.

When known, the stereochemistry at such a new center is indicated by use of the appropriate R or S symbol (see the Preamble, section 5), placed in parentheses, immediately before the name of the bivalent radical corresponding to the original aldehyde or ketone.

Example :

CH,O\ ,/H

HAOYCbC H 6 5 I

H06H

c: H OH

c1 H OH

CH,OH

1,2-O-(R)-Benzylidene-n-ghmitol

Rule Curb-33 ORTHO ESTERS

The “glycosides of ortho ester structure” are named (a) as cyclic acetals, according to Rule Garb-32, or (b) as ortho esters, according to Rule C-464.1zo, with the name of the saccharide as the first term of the name.

Examples:

H&O, ,OCH,

H O&H, c!

b H OCOCH,

A H OCOCH,

A H,O

HhO

H O’=:CH b 3

b CHaCOO H

b H OCOCH,

b HO

b H,OCOCH,

(a) 3,4-Di-O-acetyl- (a) 3,4,6-Tri-O-acetyl- 1,2-O-(l-methoxyethylidene)- 1,2-O-(l-chloro-l-methoxy-

a-D-ribopyranose methylene)-a-n-glucopyranose (b) oc-n-Ribopyranose (b) OL n-Chrcopyranose

3,4-diacetate 1,2-(methyl 3,4,6-triacetate 1,2-(methyl orthoacetate) chloroorthoformate)

Note. In each example a new asymmetric center has been introduced at the carbon atom of the hypothetical ortho acid.

When known, the stereochemistry at such a new center are indicated by use of the appropriate RS symbol (see the Preamble, section 5), placed in parentheses, immediately before that part of the name that includes the new asymmetric center.

a0 IUPAC Nomenclature of Organic Chemistry, Section C:

Examples :

a) 3,4,6-Tri-O-acetyl-l,2-0-(R)-(1-chloro-l-methoxy- methylene)-oc-n-ghicopyranose

b) a-n-Chicopyranose 3,4,6-triacetate 1,2-(R)-(methyl chloroorthoformate)

ACETALS AND THIOACETALS

Rule Carb-34

The compounds obtained by transforming the carbonyl group of a saccharide or saccharide derivative into the grouping

><

OR1 OR’ SR’ C \

OR2 ’ / or

>< C

SR2 SR2

are named by placing after the name of the saccharide or saccharide derivative the term ‘acetal’, ‘monothioacetal’ or ‘dithioacetal’ as appropriate, preceded by the names of the radicals R1 and R2. With monothioacetals the mode of bond- ing of two different radicals R1 and R2 is indicated by the use of the prefixes 0 and S.

Examples:

HWW,),

HCOH

b HO H

b H OH

HCOH

JH,OH

n-Chmose diethyl acetal

S-CH,

HC/

,BdH, HCOH

CH,OH

n-Chicose ethylene dithioacetal

HOCH I

HCOH

H&OH

b H,OH

n-Fructose diethyl acetal

SW,

HCOCH,

I HCOH

b HO H

A H OH

HCOH I CH,OH

n-Glucose S-ethyl O-methyl monothioacetal

Note. In the last example carbon atom number one has become asymmetric. When known, the stereochemistry at this new asymmetric center will be indicated by use of the Sequence Rule Symbol, R or S (see the Preamble, section 5), preceded by the locant of the new asymmetric center and both . . ^.

see ref. [I]. placed in parentheses, at the beginning of the name.


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Example:

OCH,

c!J H SCH,

& H OAc

AcOhH

c! H OAc

A H OAc

c: H,OAc

(iR)-2,3,4,5,6-Penta-acetyl-D-glucose dimethyl monothioacetal

Rule Curb-35 HEMIACETALS

The compounds obtained by transforming the carbonyl group of the acyclic form of a saccharide, or saccharide derivative, into the grouping

OR SR SR

>‘<” >c<,, ’ x0, Or >“<,H OH

are named as indicated in Rule Carb-34, by using the endings ‘hemiacetal’, ‘monothiohemiacetal’, or ‘dithiohemiacetal’, as appropriate. The two isomers of a monothiohemiacetal are differentiated by use of 0 and S prefixes.

Examples:

OW,

HCOH

I HCOCOC,H,

I C,H,COOCH

b H OCOC,H,

H&OCOC,H,

&H,oCOC,H,

2,3,4,5,6-Penta-O-benzoyl- D-glucose ethyl

hemiacetal

OC,H, I

HCSH

I HCOCOC,H,

I C,H,COOCH

1 HCOCOC,H,

d H OCOC,H,

~H,ocOC,H, 2,3,4,5,6-Penta-O-benzoyl-

D-glucose O-ethyl monothiohemiacetal

31’

SW, I

HCSH

b H OCOC,H,

C,H,COOCH I

HCOCOC$H, I

HCOCOCBH,

~JH,OCOC,H,

2,3,4,5,6-Penta-O-benzoyl- D-glucose ethyl

dithiohemiacetal

SC&

HCOH I

HCOCOC,H, I

C,H,COOCH

I HCOCOC,H,

I HCOCOC,H,

I CH,OCOC,H,

2,3,4,5,6-Penta-O-benzoyl- D-glucose S-ethyl

monothiohemiacetal

Note. In these compounds carbon atom number one has become asymmetric. When known, the stereochemistry at this new asymmetric center is indicated as described in the Note to Rule Carb-34.

OTHER, SULFUR MONOSACCHARIDES

Rule Carh-36

Replacement of a hydroxyl oxygen atom of an aldose or ketose, or of the oxygen atom of the carbonyl group of the acyclic form of an aldose or ketose, by sulfur is indicated by placing the (non-detachable) affix ‘thio’, preceded by the appropriate locant, before the systematic or trivial name of the aldose or ketose.

Replacement of the ring oxygen atom of the cyclic form of an aldose or ketose by sulfur is indicated in the same way, the number of the highest numbered carbon atom of the ring being used as locant.

Glycosides in which the glycosidic oxygen atom is replaced by sulfur are designated generically as ‘thioglycq- sides’.

Selenium compounds are named analogously, by use of the affix ‘seleno’.

Note. It should be noted that the appropriate affix is thio, not thia; the latter is used in systematic organic chemical nomenclature to indicate replacement of CH, by S.

Examples:

HC=S

I HCOAc

I CH,OAc

2 3 4 5 6-Penta- I , 9 f O-acetyl-l-thio-

aldehydo-D-glucose

HCSCH,

b H OAc

1! AcO H

b

J

H OAc

d HO

H,OAc

Methyl 2,3,4,6-tetra- O-acetyl-l-thio-

cx-D-glucopyranoside

HC=O

A H SAC

AcOCH

A H OAc

b H OAc

CH,OAc

3,4,5,6-Tetra- 0-acetyl-2-S-acetyl-2-thio-

aldehydo-D-glucose

c! HaOH

Methyl 4-seleno- oc-D-xylofuranoside


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I UPAC-I T/‘B Tentative Rules for Carbohydrate Nomenclature Vol. 247, No. 3

H&H, I

bH, I

HCOCOCH, I

HCOCOCH, I CH,OCOCH,

Methyl &seleno- cx-n-fructofuranoside

Ethyl 3,4,6,7-tetra- O-acetyl-2-deoxy-l,&dithio- a-n-gluco-heptopyranoside

INTRAMOLECULAR ANHYDRIDES

Rule Curb-37

An intramolecular ether (commonly called an intramolecular anhydride), formed by elimination of water from two alcoholic hydroxyl groups of a single molecule of a monosaccharide (aldose or ketose) or monosaccharide derivative, is named by attaching the (detachable) prefix ‘anhydro’ by a hyphen before the monosaccharide name; this prefix, in turn, is preceded by a pair of locants identifying the two hydroxyl groups involved.

Examples:

CHO

b

H,COCH

H OCH, HhOCrr,

/ n

c! H

HCO 0 I

\I

HCOCH, 0 I

\I

HCOCH,

CH, CH,

7 -CH

I HOCH

I O/cH

‘CH I

HCO- I

-OCH,

3,6-Anhydro- Methyl 3,6-an- 1,6:3,4-Dianhydro- 2,4,5-tri-o-methyl- hydro-2,5-di- @-n-talopyranose

aldehydo-D-glucose O-methyl- p-n-glucofuranoside

I.

HCOCH, I

HC,

H1,/”

I HCOCOCH,

I HCO-

I CH,OCOCH,

2,3-Anhydro- 4-O-methyl- a-n-manno-

pyranose

1,7-Anhydro- Methyl 4,6-di- D-glycero- O-acetyl- B-D-g&O- 2,3-anhydro-

heptopyranose ol-n-allopyranoside

CO,H I

H::H\O

c! HO

H f! J

b H,OH

2,5-Anhydro- n-gluconic acid

3,6-Anhydro- D-glUCOnO- 1,4-la&me

0 I HCOH

\ (4 HZ

1,4: 3,6-Dianhydro- D-g1ucito1

(not 1,4: 3,6-dianhydro-L-gulitol)

Trivial names for anhydro-monosaccharides established by usage but not recommended (because of possible confusion with polysaccharide names based on the use of the termination -an) are

,&CH,OH

/4 ObH

/ HAOH

HCO-

Levoglucosan (preferred name:

l,B-anhydro- p-n-glucopyranose)

Sedoheptulosan (preferred name:

2,7-anhydro-p-n-altro- 2-heptulopyranose)

Note. The compounds usually known as monosaccharide anhydrides, glycose anhydrides, or glycosans (whose formation involves the reducing group), as well as the anhydro sugars (whose formation does not involve the reducing group) are not here differentiated in treatment.

INTERMOLECULAR ANHYDRIDES

Rule Garb-38

An intermolecular cyclic acetal (commonly called an intermolecular anhydride), formed by condensation of two monosaccharide molecules with the elimination of two molecules of water, is named by placing the word ‘dianhydride’ after the names of the two parent monosaccharides. When the two parent monosaccharides are different, the sequence of their citation is according to the order of preference given in Rule Carb-2. The position of each anhydride link is indicated by a pair of locants showing the positions of the two hydroxyl groups involved; the locants relating to one monosaccharide (in a mixed dianhydride, the second monosaccharide named) is primed. Both pairs of locants immediately precede the word “dianhydride”.


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Examples:

bH li B Iti Di-a-n-fructopyranose 1,2’;2,1’-dianhydride

H6 bH Di-IQ-n-ribofuranose 1,5’;5,1’-dianhydride

a-n-Fructopyranose a-u-sorbopyranose 1,2’;2,1’-dianhydride

OLIGOSACCHARIDES

An oligosaccharide is a compound which, on complete hydrolysis, gives monosaccharide units only, in relatively small number per molecule (in contrast to the high-polymeric polysaccharides).

Comment. Most of the naturally occurring oligosaccharides have well-established and useful common names (for example, cellobiose, lactose, maltose, melizitose, raffinose, stachyose, and sucrose) which were assigned before their complete structures were known. Rational names may be assigned as described in the following Rules.

Rule Carb-39 DISSACHARIDES

a) Nonreducing. A nonreducing disaccharide is named, from its component monosaccharide parts, as a glycosyl glycoside.

Example:

CH,OH CH,OH

H~@“+ijf!~2~~

Sucrose: /?-D-fructofuranosyl a-n-glucopyranoside (not a-no-glucopyranosyl /z?-D-fructofuranoside;

alphabetical order of monosaccharide units, see Rule Carb-2)

b) Reducing. A reducing disaccharide is named, from its component monosaccharide parts, as a glycosylglycose.

Example:

CH,OH

a-lactose: 4-0-I%n-galactopyranosyl-a-n-glucopyranose

A reducing disaccharide may also be named according to the method described in Rule Carb-40.

Example :

a-Lactose: 0-j3-n-galactopyranosyl-(l&.4)-E-n-glucopyranose

c) Derivatives. Derivatives of disaccharides are named according to the rules for monosaccharides.

Examples :

Methyl a-lactoside: methyl 4-0-/3-n-galactopyranosyl-a-n- glucopyranoside, or methyl 0-p-n-galactopyranosyl-(1+4)- n-n-glucopyranoside 2-Amino-2-deoxy-4-0-(~-D-galactopyranosy1)-a-n-glucopyra-

nose, or @%n-ga1actopyranosyl-(l-+4)-2-amino-2-deoxy- a-n-glucopyranose

TRISACCHARIDES AND HIGHER OLIGOSACCHARIDES

Rule Garb-40

a) Nonreducing. A nonreducing trisaccharide is named as a glycosylglycosyl glycoside, from its component monosaccharide parts. Higher nonreducing oligosaccharides are named similarly.

Between the name of one glycosyl radical and the next are placed two locants which indicate the respective positions involved in this glycosidic union; these locants are separated by an arrow (pointing from the locant corresponding to the glycosyl carbon atom to the locant corresponding to the hydroxylic carbon atom involved) and are enclosed in parentheses.

Example:

H;&/&o~H20H

H OH H OH HO H

Raffinose: 0-a-n-galactopyranosyl-(1+6)-a-n-glucopyranosyl/3-n-fructofuranoside


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b) Reducing. A reducing trisaccharide is named as a glycosylglycosylglycose, from its component monosaccharide parts. Higher reducing oligosaccharides are named similarly.

Examples :

VI-&OH

H

!!I bH

&Ceiiotriose: O-/?-D-GhmopyranosyI-(1+4)-O-,&D-giucopyra- nosyl-(1+4)-a-D-glucopyranose

Ii 6H iI i)H

Panose: O-oc-D-Glucopyranosyl-(i+6)-o-~-D-glucopyranosyl- (l&+4)-oc-D-glucopyranose

SOOH

FOOH

H OH

O-(or-D-Gaiactopyranosyiuronic acid)-(1+4)-O-(a-u-galacto- pyranosyluronic acid)-(1+4)-n-D-gaiactopyranuronic acid

c) Reducing, Branched. By inserting one glycosyl substituent in brackets, it is distinguished from the second glycosyl substituent.

CH,OH

~-oc-D-~lucopyranosyl-(~~4)-~-[oc-D-glucopyranosyl- (I-+6)]-n-D-glucopyranose

Synonym: 4,6-di-o-(a-D-glucopyranosyl)-n-D-glucopyranose (preferred name)

REFERENCES

1. Nomenclature of Organic Chemistry. (a) Section A and B, 1957 (2nd edition, 1966) ; (b) Section C, 1965. Published on behalf of the International Union of Pure and Ap- plied Chemistry by Butterworths, London. [Editorial note. Section A and B are also to be found in J. Amer. Chem. Sot. 82 (1960) 5545; Section C in Pure Appl. Chem. 11 (1965) Nos 1 and 21.

2. Cahn, R. S., Ingold, C. K., and Prelog, V., Angew. Chem. 78 (1966) 413; Angew. Chem. Int. Ed. Engl. 5 (1966) 385; IUPAC Tentative Rules for the Nomenclature of Organic Chemistry, I UPAC Information Bulletin, 35 (1969) 71. [Editorial note. See also Eur. J. Biochem. 18 (1971) 1511.


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The following Tentative Rules of the IUPAC Commission for the Somenclature of Organic Chemistry (CNOC) wrd of the IUPAC-IUB Commission on Biochemical Xomenclnture (CBX), some of which arc issued jointly with the IUPAC Commission for the Nomenclature of Organic Chemistry (CNOC) are available from Waldo E. Cohn, Direct-or, NAS-XRC Oflicc: of Biochemical Nomcnclnturc, Oak Ridge N:rt,ional Laboratory, P.O. Box Y, Oak Ridge, Tennes- see 37X30, U.S.A. Joint Rules arc marked with :m asterisk.

Nomenclatuw

Komcnclaturc of vitamins, coenzymes and related compounds: Trivial names of miscclh- IICOUS compounds of importance in biochemistry; Nomcnclaturc of quinones with isoprcnoid side chains; Nomenclature and symbols for folic acid and related compounds; Komcnclnture of corrinoids [(1966) ./. Riol. Chem. 241, 2937-29441.

The nomenclature of lipids. A document, for discussion [(1967) J. Z&l. Chum. 242, 4S4;ip 48491; amendments [(1970) ,I. Bid. Chem. 245, 15113.

The nomenclature of cyclitols* [(1968) .I. Biol. Chem. 243, 5SO9-X319]. The nomenchrt ure of steroids* [( 1969) Biochemistry 8, 2227-22421; corrections [see (1970)

Eur. J. Biochem. 12, 11. Nomenclature for vitamins Be and related compourlds [(1970) .I. Biol. (‘hem. 245, 4229%

4x311. IUI’AC Tcntalive rules for the nomcnclakrrc of organic chemistry. See E. l~und:n~~cntnl

stcreochcmistry [see (1971) BUT. J. Biochcm. 18, 151; or (1970) .I. Org. Chcm. 35, 2S49-%67]. Tentntivc rules for carbohydrate nomenclature. Part I* [this document].

Abbreviations and symbols for chemical names of special interest in biological chemistry [( 1966) ,/. l3ioZ. Chem. 241, 527~5331.

12bbrcviatcd designation of amino acid derivatives and peptides [(1966) J. Biol. Chem. 241, 2491-24953.

Rules for naming syntlictic modifications of nat~urnl peptides [(1967) ./. Kiol. (‘hem. 242, 555-5571.

Abbreviated nomcnclnt.ure of synthetic polypeptides (polymerized amino acids) [(196S) ./. Riol. Chcm. 243, 2451&%4X3] ; correction [see (1970) Eur. J. B&hem. 12, I].

A one-letter not,ntion for amino acid sequences [(196S) ./. Biol. Chem. 243, 3557-35591. Abbreviations and symbols for nucleic acids, polynucleotides and their constituents [(1970)

J. Ijiol. (‘hem. 245, 5171-51761; corrections [(1971) J. Biol. Chem. 246, 43941. Abbreviations and symbols for the description of the conformation of polypeptidc chains

[(1970) .I. Z%oZ. Chcm. 245, 6489-64971.

A document, OBN-5, describing the (American) SAS-NRC Office of Biochemical Komen- clature, and listing other rules affecting biochemical nomenclature is available from its Director, Dr. Waldo IX. Cohn [see also (1967) J. Chem. Dot. 7, 721.

rlckxozcleclgment-We are indebted to the Editors and Publishers of the European Journal of Biochemist,ry for permission to reproduce this document xhich first appeared in (1971) Eur. .I. Biochpm. 21 455-477. , , , < I


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IUPAC-IUB Commission on Biochemical Nomenclature (CBN)IUPAC Commission on the Nomenclature of Organic Chemistry (CNOC) and

Tentative Rules for Carbohydrate Nomenclature: Part 1, 1969

1972, 247:613-635.J. Biol. Chem.

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Tentative Rules for Carbohydrate Nomenclature · Tentative Rules for Carbohydrate Nomenclature Part 1, 1969 ... aspects of the nomenclature of carbohydrates ... the carbonyl group