CarbohydrateChemistryPart1:SimpleCarbohydrates

Dr.KevinAhern

Outline

• Nomenclature• Structures• Cyclizations• Modifications

SimpleCarbohydrates

Saccharides

Monosaccharides

Saccharides

Monosaccharides

• Cx(H2O)x• Glucose(C6H12O6)

• Fructose(C6H12O6)

• Ribose(C5H10O5)

• Galactose(C6H12O6)

• Glyceraldehyde(C3H6O3)

Saccharides

Monosaccharides

• Cx(H2O)x• Glucose(C6H12O6)

• Fructose(C6H12O6)

• Ribose(C5H10O5)

• Galactose(C6H12O6)

• Glyceraldehyde(C3H6O3)

X =

Saccharides

Monosaccharides

• Cx(H2O)x• Glucose(C6H12O6)

• Fructose(C6H12O6)

• Ribose(C5H10O5)

• Galactose(C6H12O6)

• Glyceraldehyde(C3H6O3)

• Tri- = 3 • Tetr- = 4 • Pent- = 5 • Hex- =6 • Hept- = 7 • Oct- = 8

X =

Saccharides

Monosaccharides

• Cx(H2O)x• Glucose(C6H12O6)

• Fructose(C6H12O6)

• Ribose(C5H10O5)

• Galactose(C6H12O6)

• Glyceraldehyde(C3H6O3)

• Tri- = 3 • Tetr- = 4 • Pent- = 5 • Hex- =6 • Hept- = 7 • Oct- = 8

X =

Aldehydes = Aldoses Ketones = Ketoses

Saccharides

DifferentSizesThe-oses

D-GlyceraldehydeD-Threose

D-Ribose

D-Glucose

DifferentSizesThe-oses

D-GlyceraldehydeD-Threose

D-Ribose

D-Glucose

3 Carbons

Triose

DifferentSizesThe-oses

D-GlyceraldehydeD-Threose

D-Ribose

D-Glucose

3 Carbons

Triose

4 Carbons

Tetrose

DifferentSizesThe-oses

D-GlyceraldehydeD-Threose

D-Ribose

D-Glucose

3 Carbons

Triose

4 Carbons

Tetrose

5 Carbons

Pentose

DifferentSizesThe-oses

D-GlyceraldehydeD-Threose

D-Ribose

D-Glucose

3 Carbons

Triose

4 Carbons

Tetrose

5 Carbons

Pentose

6 Carbons

Hexose

CommonSugarsAldoseandKetose

CommonSugarsAldoseandKetose

D-Glucose

CommonSugarsAldoseandKetose

D-Glucose D-Fructose

CommonSugarsAldoseandKetose

D-Glucose D-Fructose

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CommonSugarsAldoseandKetose

D-Glucose D-Fructose

AldehydeKetone

CommonSugarsAldoseandKetose

D-Glucose D-Fructose

AldehydeKetone

Aldose Ketose

SimpleSugars

SimpleSugars

Aldopentose

SimpleSugars

Aldopentose Aldohexose

SimpleSugars

Aldopentose Aldohexose Ketohexose

SimpleSugars

Aldopentose Aldohexose Ketohexose Aldohexose

SimpleSugars

Aldopentose Aldohexose Ketohexose Aldohexose Aldohexose

SimpleSugars

Aldopentose Aldohexose Ketohexose Aldohexose Aldohexose

AsymmetricCarbonsTheGlyceraldehydes

AsymmetricCarbonsTheGlyceraldehydes Asymmetric

PenultimateCarbon

AsymmetricCarbonsTheGlyceraldehydes Asymmetric

PenultimateCarbon

L- Configuration

AsymmetricCarbonsTheGlyceraldehydes Asymmetric

PenultimateCarbon D- Configuration

L- Configuration

AsymmetricCarbonsTheGlyceraldehydes Asymmetric

PenultimateCarbon D- Configuration

L- ConfigurationMirror Images

AsymmetricCarbonsTheGlyceraldehydes Asymmetric

PenultimateCarbon D- Configuration

L- Configuration

L-Glyceraldehyde D-Glyceraldehyde

MultipleAsymmetricCenters• Glucose

D-Glucose

MultipleAsymmetricCenters• Glucose

D-Glucose

Asymmetric Carbons

MultipleAsymmetricCenters• Glucose

D-Glucose

D-configuration

Enantiomers• Mirror Images

D-Glucose L-Glucose

Enantiomers• Mirror Images

D-Glucose L-Glucose

D-configuration

Enantiomers• Mirror Images

D-Glucose L-Glucose

D-configuration L-configuration

Diastereomers• Same chemical type & size, non-mirror images

D-Glucose D-Gulose

Diastereomers• Same chemical type & size, non-mirror images

D-Glucose D-Gulose

Same Configuration

Same Configuration

Diastereomers• Same chemical type & size, non-mirror images

D-Glucose D-Gulose

Same Configuration

Same Configuration

Different Configurations

Epimers• Diastereomers differing in configuration of one carbon only

D-Glucose D-Galactose

CyclizationofSugars

In Close Spatial Proximity

CyclizationofSugars

CyclizationofSugars

New Asymmetric Center

CyclizationofSugars

New Asymmetric Center

The New Asymmetric Carbon Is Called Anomeric

CyclizationofSugars

CyclizationofSugars

CyclizationofSugars

CyclizationofSugars

HaworthStructures• Glucose

α-D-Glucopyranose β-D-Glucopyranose

HaworthStructures• Glucose

α-D-Glucopyranose β-D-Glucopyranose

HaworthStructures• Glucose

α-D-Glucopyranose

Anomers

β-D-Glucopyranose

CommonFuranoses• Fructose and Ribose

β-D-Fructofuranose β-D-Ribofuranose

ConformationalIsomers• Chair and Boat Forms of β-D-Glucose

ConformationalIsomers• Chair and Boat Forms of β-D-Glucose

CyclicStructures• Glucose

ModifiedSugars

Galactosamine N-acetylglucosamine Mannose-6-phosphate

Fructose-1,6-bisphosphate Glucuronic Acid

Glycosides

SugarAlcohol

Sorbitol (Glucitol)

ArtificialSweeteners

Sucralose

Disaccharides

• Sucrose(glucose+fructose)• Lactose(glucose+galactose)• Maltose(glucose+glucose)

Polysaccharides

• Cellulose• Glycogen• Amylose• Amylopectin• Chitin

MetabolicMelody

Hark the Sucrose(to the tune of "Hark the Herald")

Copyright © Kevin Ahern

Carbohydrates all should sing Glory to the Haworth ring

Anomeric carbons hide When they're in a glycoside

Glucopyranose is there In the boat or in the chair

Alpha, beta, D and L Di-astere-omer hell

Alpha, beta, D and L Di-astere-omer hell