Carbohydrate Structure

Biochemistry Free For All

Outline
Simple Carbohydrates

• Nomenclature
• Structures
• Cyclizations
• Modifications
 Saccharides
Monosaccharides

• Cx(H2O)x
• Glucose (C6H12O6)
• Tri- = 3
• Fructose (C6H12O6) • Tetr- = 4
• Pent- = 5
• Ribose (C5H10O5) X= • Hex- =6
• Galactose (C6H12O6) • Hept- = 7
• Oct- = 8
• Glyceraldehyde (C3H6O3)

Aldehydes = Aldoses
Ketones = Ketoses
Different Sizes
The -oses

3 Carbons 4 Carbons 5 Carbons 6 Carbons

D-Glyceraldehyde
Triose D-Threose
Tetrose
D-Ribose
Pentose
D-Glucose
Hexose
 Common Sugars
Aldose and Ketose

Aldehyde
Ketone

{ }
D-Glucose D-Fructose
Aldose Ketose
Simple Sugars

Aldopentose Aldohexose Ketohexose Aldohexose Aldohexose

 Asymmetric Carbons
The Glyceraldehydes Asymmetric
Penultimate
Carbon D- Configuration

Mirror Images
L- Configuration

L-Glyceraldehyde D-Glyceraldehyde
Multiple Asymmetric Centers
• Glucose

D-configuration

Asymmetric
Carbons

D-Glucose
 Enantiomers
• Mirror Images

D-configuration L-configuration

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

Same Configuration

Different
Configurations

Same Configuration

D-Glucose D-Gulose
Epimers
• Diastereomers differing in configuration of one carbon only

D-Glucose D-Galactose
Cyclization of Sugars

New Asymmetric Center

In Close
Spatial Proximity

The New Asymmetric Carbon

Is Called Anomeric
Cyclization of Sugars
Cyclization of Sugars
Haworth Structures
• Glucose

Anomers

 -D-Glucopyranose -D-Glucopyranose
Common Furanoses
• Fructose and Ribose

β-D-Fructofuranose β-D-Ribofuranose
Conformational Isomers
• Chair and Boat Forms of β-D-Glucose
Cyclic Structures
• Glucose
Modified Sugars

Galactosamine N-acetylglucosamine Mannose-6-phosphate

Fructose-1,6-bisphosphate Glucuronic Acid

Glycosides
Sugar Alcohol

Sorbitol (Glucitol)
Artificial Sweeteners

Sucralose
Disaccharides

• Sucrose (glucose + fructose)

• Lactose (glucose + galactose)
• Maltose (glucose + glucose)
Polysaccharides

• Cellulose
• Glycogen
• Amylose
• Amylopectin
• Chitin
 Hark the Sucrose
(to the tune of "Hark the Herald")
Copyright © Kevin Ahern
Metabolic Melody

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
Nomenclature

Fischer Form Haworth Form

Disaccharides

• Sucrose (glucose + fructose)

• Lactose (glucose + galactose)
• Maltose (glucose + glucose)
Disaccharides
• Comprised of two sugars
6
α1, β2 Diglycosidic Links
6 5

1 Glucose 4 1
3 2
5

4
1 2 5
2 6
3 4
3
6
Fructose 5 2

4 3

Glucose Fructose 1

Sucrose Sucrose
α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside
Disaccharides
• Lactose and Maltose

Glucose
Glucose Glucose
6
Galactose
6 6
5

6 4 1 5 5
2
4 1 4 1
5 3
2 2
4
1 3 3
2
3

β-1,4 Glycosidic Bond α-1,4 Glycosidic Bond

Lactose Maltose

β-D-galactopyranosyl-(1→4)-D-glucose α-D-glucopyranosyl-(1→4)-D-glucose
Reducing Versus Non-Reducing Sugars
Oligosaccharides

• Found in glycoproteins
• Play roles in cellular identity
Polysaccharides

• Cellulose
• Glycogen
• Amylose
• Amylopectin
• Chitin
Polysaccharides
• Sugar Polymers With Glycosidic Bonds
β-1,4 Glycosidic Links

Glucose Glucose

Cellulose
Polysaccharides
• Sugar Polymers With Glycosidic Bonds

α-1-4 Glycosidic Links

4 1 4 1 4 1

Glucose Glucose Glucose

Amylose - component of starch

Polysaccharides

Amylose - component of starch

Polysaccharides

α-1,6 Glycοsidic Link Branches

α-1,4 Glycosidic Links

Glucose 1 1 Glucose

6 6

4 1 4 1 4 1

Glucose Glucose Glucose

Amylopectin - component of starch

 α1,6 links
Polysaccharides
• Sugar Polymers With Glycosidic Bonds

α1,4 links
Glucose Glucose

Glucose Glucose Glucose

Glycogen
Modified Polysaccharides

Chitin in the wing

Chitin of a sap beetle
Modified Polysaccharides

Pectin - gelling agent Galacturonic acid polymer

α-1,4 bonds
Polysaccharides Binding

Lectins - proteins that bind carbohydrates specifically

Part of innate immune system
Mannose binding lectin targets microbes
Phytohemagglutinins in plants
Used by bacteria/viruses for cellular attachment
Tamiflu inhibits neuraminidase necessary for exit of flu virus
Glycolipids
• Glycoglycerolipids and Glycosphingolipids
Glycolipids
• Glycoglycerolipids

Sugar

Diacylglycerol
Glycolipids
• Glycosphingolipids

Single Sugar
Sphingolipid Backbone

Cerebrosides
Glycolipids
• Glycosphingolipids Complex Carbohydrate

Sphingolipid Backbone

Gangliosides
Glycosylation
Glycosaminoglycans - polyanionic polymers of modified sugars
Peptidoglycans - peptides/proteins linked to polyanionic polymers of modified
sugars
Glycoproteins - proteins linked to oligosaccharides
N-linked - joined to asparagine in protein - E.R. and Golgi apparatus
O-Linked - joined to serine/threonine in protein - Golgi apparatus
Glycosylation - glycoproteins
Glycosylation - Blood typing
Glycosaminoglycans
• Unbranched polyanionic saccharide polymers

Chondroitin Sulfate

Heparin
 Structural Lullaby
(To the tune of "Brahms' Lullaby")
Copyright © Kevin Ahern

Metabolic Melody
In your sleep
You can keep
Learning more about sugars
Fischer schemes
Haworth rings
D & L and everything

Hydroxides
Can’t collide
Fav’ring chair over boat form
Spatial guides
Coincide
With the way structures form