WELLCOME IN BIOCHEMISTRY

CHEMISTRY OF CARBOHYDRATES

Carbohydrates y
Biological importance. Definition Classification & examples for each class Describe their structure

Dr: AbouSree Ellethy College of Dentistry Biochemistry

Importance of carbohydrates:
Carbohydrates (glycans)

Definition
are organic compounds that are

They provide human body with energy. Regulation of metabolic processes in the body body. Help in cell membranes structure. Share nucleic acids (ribose and deoxyribose). Play a role in communication between cell types. Contribute structural component of different organisms like bacteria and plants p Stabilization of protein structures as in the case of glycoproteins.

polyhydroxy aldehydes or polyhydroxy ketones. Simplest carbohydrate molecule is a monosaccharide : (C-H2O)n : It has 3 to 7 carbons Either aldehyde or ketone group and hydroxyl (OH) groups on t e a de yde o eto e g oup a d yd o y (O ) g oups o nearly every carbon

I- Classification of carbohydrates
Polyhydroxyaldehydes Polyhydroxyketone
Monosaccharides: Simple sugars with multiple OH (monoses or glycoses)

Trioses, tetroses, pentoses, hexoses Oligosaccharides Di, tri, tetra, penta, up to 9 or 10 The most important is the Disaccharides, 2 monosaccharides covalently linked together. Polysaccharides or Glycans Glycans, chains of monosaccharide or disaccharide units

Ribose

Galactose G l

Glucose

Ftuctose F

Monosaccharides

Monosaccharides (CnH2nOn)
It classified by the number of carbon atoms: Triose (3 C atoms) Tetrose (4 C atoms) Pentose (5 C atoms) Hexose (6 C atoms)

Aldoses (e g glucose) have an (e.g., aldehyde group at one end.

H C H HO H H C C C C OH H OH OH O

Ketoses (e g fructose) have (e.g., a keto group at C2.

C H 2O H C HO H H C C C O H OH OH

C H 2O H

C H 2O H

D -glucose

D -fructose fructose

Monosaccharide (CnH2nOn)
It classified by th number of carbon atoms l ifi d b the b f b t
No of C 3 4 5 6 7 Nomenclature Trioses Tetrose Pentose Hexose Heptose Aldehyde Glycerose Erythrose Ribose Glucose Sedoheptose Ketone Dihydroxyacetone Erythrulose Ribulose Fructose Sedoheptulose

Chiral Objects
A chiral carbon atom has four different groups attached Chiral compounds have the same number of atoms arranged differently in space space.
Sugars with more than one Suga s w t oe t a o e
O H O H C H C OH HO C H H C OH H C OH CH 2 OH g ucose D -glucose C HO C H H C OH HO C H HO C H CH 2 OH g ucose L -glucose
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chiral center, D or L refers to the asymmetric C farthest from the aldehyde or keto group.

Epimers:
Isomers as a result of variations in configuration of the OH and H on C2, C3, & C4 of glucose. e.g. epimers of Gl i f Glucose Mannose and Galactose, formed by ep e at o at C2 and C4, ose a d G c ose o ed epimerization C a d C , respectively
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Enantiomers
The orientation of OH groups around C atom adjacent to the terminal primary alcohol gives 2 isomers (Enantiomers).
1

D-Galactose

D-Mannose

D-Glucose

Optical activity
Presence of asymmetric carbon atoms gives Optical isomer. P l i d li ht rotates t the right, dextrorotatory (+) or to left, Polarized light t t to th i ht d t t t t l ft

II- Oligosaccharides g
They are composed of 2-10 monosaccharide residues linked by a 2 10 glycoside bond. Hydrolysis yields 2-10 similar or different monosaccharides . Most common is Disaccarides with general formula CnH2n-2On-1.

levorotatory ()
Most naturally occurring sugars are D isomers.

L-Glucose

D-Glucose

Examples of Disaccharide
Most common are the disaccharides are (Sucrose, lactose, and ( , , maltose). 1- Sucrose hydrolyzes to Glucose + Fructose molecules 2 2- Lactose hydrolyzes to Glucose + Galactose molecules 3- Maltose hydrolyzes to 2 molecules of D-glucose molecules Sucrose, (12) , ( ) Maltose, (14) , ( )

Lactose, (14)

Polysaccharides
Polysaccharides are condensation products of more than 10 monosaccharide units with general formula (C6H10O5)n . They include:
Homopolysaccharides (composed of a single monosaccharide) e.g. Starch, Glycogen, Inulin, Cellulose p y ( p ) Heteropolysaccharides (composed of different monosaccharides) e.g. Heparin & chondroitin sulphate Complex carbohydrates e.g. Mucopolysaccharides (Glycosaminoglycans) when attached to

1-Glycogen y g
Is highly branched polysaccharide that stores -D-glucose in muscle and contains both (1 4) links and (1 6) branches. t i b th (1,4) li k d (1,6) b h It is hydrolyzed by both and -amylases and by glycogen phosphorylase to give glucose.
(1,4) links

proteins, proteins they form proteoglycans proteoglycans.

(1,4) links

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2-Cellulose 2 C ll l
It is Polymer of b-D-Glucose with -1,4-glycosidic bonds. y , gy It cannot be digested by humans because humans cannot break down 1,4-glycosidic bonds.

3- Starch
It is composed of 30% amylose and 70% amylopectin in plants. Made of amylose and amylopectin. d f l d l i
1-Amylose : Polymer of -D- Glucose -1,4 glycosidic bonds . 2-Amylopectin: branched-chain polymer of -D-glucose with -1,4-and -1,6 glycosidic bonds
CH 2 OH O OH O O OH OH OH CH 2 OH O OH CH 2 OH O

CH 2 OH O OH OH OH

O
OH

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4- Dextran (Glucosan) ( )
It is similar to amylopectin, but the main chains are formed by 16
glycosidic linkages and the side branches are attached by 13 or 14 linkages.

5- Inulins (fructans)
They are polymers consisting of fructose units that typically have a terminal glucose. t i l l They are nondigestible by human intestinal enzymes, but they are totally fermented by colonic microflora.

It is an oral bacterial product that adheres to the teeth, creating a film called plaque plaque.