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ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS Vol. 220, No. 1, January, pp. 330-332, 1983 Polysaccharide Nomenclature Recommendations 1980* IUB-IUPAC JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE (JCBN) CONTENTS 1. Genetic terms 2. The meaning of -an 3. Configuration of units 4. Naming newly discovered polysaccharides 5. Uranic acid derivatives 6. Amino deoxysugar derivatives 7. Polysaccharides composed of more than one kind of resi- due 6. Designation of linkage 9. Substituted residues 10. Glycoproteins, proteoglycans. and peptidoglycans Polysaccharide nomenclature follows the general principles of established organic (1) and carbohydrate (2) nomenclature. For abbreviated nomenclature, see either Abbreviated Ter- minology o/Oligosaccharide Chatns, a document being pub- lished at the same time as this one, for a symbolism that explicitly gives all structural features known, or its Appendix (alternatively Section Lip-3 of Nomenclature of Lipids (3)) for a more condensed symbolism. Examples of both symbolisms are given herein. 1. Polysaccharide (glycan) is the name given to a macro- molecule consisting of a large number of monosaccharide (glycose) residues joined to each other by glycosidic linkages. The term poly(g1ycos.e) is not quite a synonym for polysac- charide (glycan) (cf Nomenclature of Regular Single Strand Organic Polymers (4)), because it includes macromolecules composed of glycose residues joined to each other by nongly- cosidic linkages. Note-Polysaccharides may be linear, branched, or cyclic. Although most polysaccharides bear a reducing monosaccha- ride residue at one end, and are, therefore, reducing polysac- charides, some polysaccharides have nonreducing residues at both ends. For polysaccharides containing a substantial .proportion of amino sugar residues, the term polysaccharide is adequate, although the term glycosaminoglycan may be used where particular emphasis is desired. Polysaccharides composed of only one kind of monosaccha- ride are described as homopolysaccharides (homoglycans). Similarly, if two or more different kinds of monomeric unit are present, the class name of heteropolysaccharide (hetero- glycan) may be used. * Document of the IUB-IUPAC Joint Commissmn on Bmchemical Nomenclature (JCBN) whose members are P. Karlson (Chauman). H. B. F. Dixon, Y. Jeannin. C. Li6becq (as Chauman of the IUB Committee of Editors of Biochemical Journals). B. Lindberg, K. L. Loenmg, G. P. Moss, and S. F. Velick. in consultation with J. F. G. Vliegenthart and the Nomenclature Committee of IUB. whose addi- tional members are H. Bielka. W. B. Jakoby. B Keil. and E. C. Webb. Comments or suggestions for modifications may be sent to the sec- retary of JCBN, H. B. F. Dixon. Department of Biochematry. Tennis Court Road. Cambridge. United Kingdom CB2 IQW. or to any member. JCBN thanks the expert panel of B. Lindberg (convener), D. Horton, the late W. Klyne. K. L. Loening. D. J. Manners. W. G. Overend. H. Paulsen. D. A. Rees. and R. S Twon for drafting these proposals. The term oligosaccharide is commonly used for carbohy drates comprised of 2 to about 10 monosaccharide residues. 2. A polysaccharide (glycan) composed of a single type of monosaccharide residue will be named, as a general term, by replacing the ending “ose” of the sugar by the suffi “an.” Note-Examples of established usage of the “an” ending are: xylan for polymers of xylose, mannan for polymers of mannose, and galactan for polymers of galactose. Cellulose and starch are both glucans, as they are composed of glucose residues. 3. When the configurational series of the monomer residues is shown, “D” or "L" may be included in the name of the polysaccharide. Examples: A o-glucan (nigeran) -5).a-~-A&(1 - 5).a-L-Araf-(1 + 5).a+Araf-(I - 5).a-L-A&(& 3 3 T t 1 1 a-L-A& Q-L-Ara/ An L-arabinan’ (from mustard seeds) 4. Names assigned to newly discovered polysaccharides should end in “an.” Example: Pustulan (a glucan from the lichen Umbrlrcanapusfulata) Note-The name ending in “an” refers to the unsubstituted polysaccharide. Thus xylan occurs in nature in unacetylated and partially acetylated forms. Xylan designates unacetylated xylan, and xylan acetate an acetylated xylan. 5. A polysaccharide (glycan) composed entirely of glycu- ronic acid residues is named by replacing “ic acid” by “an.” The generic name for this group is “glycuronan.” Example: C02H -0 0 + CO*H OH 0 0 + OH CO*H OH 0 0 Q- OH OH bli A D-galacturonan (pectic acid) Note-The term glycuronan is used instead of “polyuron- ide,” as the latter term is incorrect. 6. A polysaccharide composed entirely of amino sugar res- idues is named by the systematic nomenclature pertinent to the amino sugar. ’ Several of the polysacchandes m the examples have less-ordered structures. In the structural formulas given for these. the main sugar components and linkages are given, hut not thev proportmns 330 Copyright 0 196.3 by Academic Press, Inc. All rights of reproduction in any form reserved.

Polysaccharide nomenclature: Recommendations 1980

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ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS

Vol. 220, No. 1, January, pp. 330-332, 1983

Polysaccharide Nomenclature Recommendations 1980*

IUB-IUPAC JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE (JCBN)

CONTENTS

1. Genetic terms 2. The meaning of -an 3. Configuration of units 4. Naming newly discovered polysaccharides 5. Uranic acid derivatives 6. Amino deoxysugar derivatives 7. Polysaccharides composed of more than one kind of resi-

due 6. Designation of linkage 9. Substituted residues

10. Glycoproteins, proteoglycans. and peptidoglycans

Polysaccharide nomenclature follows the general principles of established organic (1) and carbohydrate (2) nomenclature. For abbreviated nomenclature, see either Abbreviated Ter- minology o/Oligosaccharide Chatns, a document being pub- lished at the same time as this one, for a symbolism that explicitly gives all structural features known, or its Appendix (alternatively Section Lip-3 of Nomenclature of Lipids (3)) for a more condensed symbolism. Examples of both symbolisms are given herein.

1. Polysaccharide (glycan) is the name given to a macro- molecule consisting of a large number of monosaccharide (glycose) residues joined to each other by glycosidic linkages. The term poly(g1ycos.e) is not quite a synonym for polysac- charide (glycan) (cf Nomenclature of Regular Single Strand Organic Polymers (4)), because it includes macromolecules composed of glycose residues joined to each other by nongly- cosidic linkages.

Note-Polysaccharides may be linear, branched, or cyclic. Although most polysaccharides bear a reducing monosaccha- ride residue at one end, and are, therefore, reducing polysac- charides, some polysaccharides have nonreducing residues at both ends.

For polysaccharides containing a substantial .proportion of amino sugar residues, the term polysaccharide is adequate, although the term glycosaminoglycan may be used where particular emphasis is desired.

Polysaccharides composed of only one kind of monosaccha- ride are described as homopolysaccharides (homoglycans). Similarly, if two or more different kinds of monomeric unit are present, the class name of heteropolysaccharide (hetero- glycan) may be used.

* Document of the IUB-IUPAC Joint Commissmn on Bmchemical Nomenclature (JCBN) whose members are P. Karlson (Chauman). H. B. F. Dixon, Y. Jeannin. C. Li6becq (as Chauman of the IUB Committee of Editors of Biochemical Journals). B. Lindberg, K. L. Loenmg, G. P. Moss, and S. F. Velick. in consultation with J. F. G. Vliegenthart and the Nomenclature Committee of IUB. whose addi- tional members are H. Bielka. W. B. Jakoby. B Keil. and E. C. Webb. Comments or suggestions for modifications may be sent to the sec- retary of JCBN, H. B. F. Dixon. Department of Biochematry. Tennis Court Road. Cambridge. United Kingdom CB2 IQW. or to any member. JCBN thanks the expert panel of B. Lindberg (convener), D. Horton, the late W. Klyne. K. L. Loening. D. J. Manners. W. G. Overend. H. Paulsen. D. A. Rees. and R. S Twon for drafting these proposals.

The term oligosaccharide is commonly used for carbohy drates comprised of 2 to about 10 monosaccharide residues.

2. A polysaccharide (glycan) composed of a single type of monosaccharide residue will be named, as a general term, by replacing the ending “ose” of the sugar by the suffi “an.”

Note-Examples of established usage of the “an” ending are: xylan for polymers of xylose, mannan for polymers of mannose, and galactan for polymers of galactose. Cellulose and starch are both glucans, as they are composed of glucose residues.

3. When the configurational series of the monomer residues is shown, “D” or "L" may be included in the name of the polysaccharide.

Examples:

A o-glucan (nigeran)

-5).a-~-A&(1 - 5).a-L-Araf-(1 + 5).a+Araf-(I - 5).a-L-A&(& 3 3 T t 1 1

a-L-A& Q-L-Ara/

An L-arabinan’ (from mustard seeds)

4. Names assigned to newly discovered polysaccharides should end in “an.”

Example:

Pustulan (a glucan from the lichen Umbrlrcanapusfulata)

Note-The name ending in “an” refers to the unsubstituted polysaccharide. Thus xylan occurs in nature in unacetylated and partially acetylated forms. Xylan designates unacetylated xylan, and xylan acetate an acetylated xylan.

5. A polysaccharide (glycan) composed entirely of glycu- ronic acid residues is named by replacing “ic acid” by “an.” The generic name for this group is “glycuronan.”

Example:

C02H

-0 0

+

CO*H OH

0 0

+

OH CO*H

OH 0 0

Q-

OH

OH

bli A D-galacturonan (pectic acid)

Note-The term glycuronan is used instead of “polyuron- ide,” as the latter term is incorrect.

6. A polysaccharide composed entirely of amino sugar res- idues is named by the systematic nomenclature pertinent to the amino sugar.

’ Several of the polysacchandes m the examples have less-ordered structures. In the structural formulas given for these. the main sugar components and linkages are given, hut not thev proportmns

330

Copyright 0 196.3 by Academic Press, Inc. All rights of reproduction in any form reserved.

NOMENCLATURE ANNOUNCEMENTS 331

Example:

A 2.acetamido-2.deoxy-o-glucan (chitin)

7. A heteropolysaccharide (heteroglycan) is a polymer con- taining two or more kinds of sugar (glycose) or modified sugar (for example, aminodeoxyglycose or glycuronic acid) residue. When the polysaccharide has a principal chain (“backbone”) composed of only one type of sugar residue, this sugar residue should be written last, with the other sugar residues present listed in alphabetical order. However, when no single type of sugar residue constitutes the principal chain, all sugar residues should be given alphabetically, and the name terminated with the suffix glycan.

Examples:

9. When substitution occurs in a polysaccharide (glycan), each substituted type of residue is made part of the name and placed in alphabetical order.

Examples:

OH

m 0 Me

H02C

(4.O-Methyl-o-D-glucurono).D-rylan (from birch, BeluIa)

~4)-~-o-Manp-(l + 4).P-o-Msnp-(I + 4).fl-o-Manp-(I + 41.P-D-Manp-(l- 6 6

t T 1 1

0.0.Gdp a-D-Gdp

A D-gdacto-o.mannan @uaran)

(A less branched n-galacto-D-mannan could be shown in the condensed system as: [4Manpl-],4(Galal-6)Manpl- [4Manpl-],4(Calal-6)ManS1-. Note that in the condensed system repeating units are in square brackets and branches in parentheses.)

-6).WD-G&-(1 -V 6).a-r&alp-(1 - 6).~~-Galp-(l - 6).u-o-Galp(l- 2 2

T T 1 1

o-L-Fucp a-L-FUcp 3

An L-fuco-D-manno-D-galactan (from a fungus)

-4Man~l-4Glc~l-4~Galol-6~Man~l-4Man~l-

A D-galacto-D-gluco-D-mannoglycan (from softwood)

8. When the major linkage contained in a homopolysac- charide is known, an indication of it may be included in the name. The linkage designation shows the carbon atoms in- volved in the glycosidic bonds. When specific sugars are designated, notation for glycosidic linkages should precede the symbols designating the configuration of the sugar; thus, (1 -V 4)-a-D-ghC&ID.

Examples:

HO (2 -+ I)-8-D.Fnxtohranan (indin)

-4)-a-D-&p-(1 - 4)-a-M&,-(1 + 4)-o-D-Gkp(l-

OAc

2.3.Di-0.acetyl-6.0.tritylamylose

10. Polymers containing covalently bound monosaccharide and amino-acid residues are termed blycoproteins. proteogly- cans, and peptidoglycans.

Note-It is not possible to give precise distinctions between these polymers. In general terms, glycoproteins are conjugated proteins containing either oligosaccharide groups or polysac- charide groups having a fairly low relative molecular mass. Proteoglycans are proteins linked to polysaccharides of high molecular mass. Peptidoglycans consist of polysaccharide chains covalently linked to peptide chains. Such products are components of bacterial cell walls.

REFERENCES

1. International Union of Pure and Applied Chemistry (1979) No- menclature of Organic Chemistry. Pergamon. Oxford

2. Tentative Rules for Carbohydrate Nomenclature, 1969. Brochem- ical Nomenclature and Related Documents. 3rd Ed, 1978. ILJB, pp. 174-195; Biochem. J. X25.673-695 (1971); Biochemistry 10. 3985-4004 and 4995 (1971); Biochrm. Eiophys. Acto 244, 223-

332 NOMENCLATURE ANNOUNCEMENTS

302 (1971); Eur. J. Biochrm. 21, 455-477 (1971); J. Biol. Chem. them. J. 171, 21-35 (1976); Eur. J. Bwchrm. 79, II-21 (1977); 247,613~635 (1972) Hoppe&yler’s Z. Physiol. Chem. 308,617~631 (1977)

3. The i%menclalure of Lipids, 1976. Biochemical Nomeneloture 4. Nomenclature of Regcrlar Single-Strand Organic Polymers and Related Documents. 3rd Ed, 1976. IUB. pp. 122-132; Bio. 11976) Pure Appl. Chem. 43,375~385