Carbohydrates

Carbohydrates
 Carbohydrates are polyhydroxy
aldehydes or ketones, or substances that
yield such compounds on hydrolysis.
 Made up of carbon, hydrogen and
oxygen.
 C:H:O ratio usually is 1:2:1 (e.g. glucose
C6H12O6).
 Some of them contain N, P and S.
 Functions of carbohydrates in
biological systems
1. Serving as carbon and energy source (e.g. glucose)
2. Constitution of DNA and RNA (ribose and deoxyribose)
3. Central part of the metabolism of photosynthetic
organisms
4. Structural and supportive components of the cell wall
(algae, fungi and bacteria)
5. As food reserve (e.g. starch, glycogen)
6. Serving to provide adhesion between cells
7. Serving to confer biological specificity on the surface of
cells
8. Synthesis of various metabolites in the cells
 Classification of carbohydrates
Carbohydrates are broadly classified into 3 major
groups:
 Monosaccharides: Simple sugars containing 3-9 carbon
atoms; consisting of a single polyhydroxy aldehyde or
ketone unit. e.g. glucose, fructose, galactose.
 Oligosaccharide: Carbohydrates containing 2-7
monosaccharides linked together by covalent bonds
(glycosidic bonds) through a condensation reaction. e.g.
sucrose, lactose.
 Polysaccharides: Carbohydrates containing 8 or more
monosaccharides. e.g. starch, cellulose.
 Monosaccharides
• Monosaccharides have molecular formulas that are
usually multiples of CH2O
• Glucose (C6H12O6) is the most common monosaccharide
• Monosaccharides are classified by
– The location of the carbonyl group (as aldose or ketose)
– The number of carbons in the carbon skeleton
Aldoses & Ketoses
Sugars made from aldehydes form aldoses

Sugars made from ketones form ketoses

6
Important Aldoses To Study
6-C sugars

5-C
sugar
All begin with CHO group

7
Important Aldoses To Study
6-C sugars

5-C
sugar
All end with group

8
Important Aldoses To Study
6-C sugars

5-C
sugar
Most names end with -ose suffix

9
Important Ketoses To Study

3-C
sugar
5-C
sugar 6-C
sugar

Most names all end with -ulose suffix

10
 Important Ketoses To Study

3-C
sugar
5-C
sugar 6-C
sugar

Ketoses begin with group

11
 Important Ketoses To Study

3-C
sugar
5-C
sugar 6-C
sugar

Most ketoses end with group

12
 Monosaccharides
Aldoses (e.g., glucose) Ketoses (e.g., fructose) have
have an aldehyde group at a keto group, usually at C2.
one end.
H O
C CH2OH

H C OH C O

HO C H HO C H

H C OH H C OH

H C OH H C OH

CH2OH CH2OH

D-glucose D-fructose
 Monosaccharides

Monosaccharide Aldose Ketose

Triose (3C) Glyceraldehyde Dihydroxyacetone
Tetrose (4C) Erythrose ---------
Pentose (5C) Ribose, Xylose Ribulose, Xylulose
Hexose (6C) Glucose Fructose
Heptose (7C) ----------- Seduheptulose
 Oligosaccharides

Classification:
 Disaccharides: Two monosaccharides covalently
linked
 Trisaccharides: Three monosaccharides covalently
linked
e.g. Raffinose= Glucose+ Fructose + Galactose
 Polysaccharides
Classification:
 Homopolysaccharides: They contain
monosaccharide residues/ units of single type.
e.g. starch, cellulose, glycogen, chitin.

 Heteropolysaccharides: They contain 2 or more

monosaccharide residues or their derivatives. e.g.
peptidoglycan, hemicellulose, pectin.
 Isomers
• Isomers are different compounds that have the same
chemical formula

C6H12O6
17
 Enantiomers

Know this
structure

Most sugars are found in the D-stereoisomer.

D-Glyceraldehyde is the most simple aldose.

18
 D and L isomers
• The D and L isomers are mirror images of each other.
The orientation of –H and –OH groups around carbon
5 that is adjacent to primary alcohol carbon
determines whether the sugar is D- or L- isomer.
• If the –OH group is on the right side, the sugar is of D-
series and if on the left side, it belongs to L-series.
• The naturally occurring monosaccharides are mostly
of D-configaration.
 Epimers

EPIMERS- refer to sugars whose configuration differ around

one specific carbon atom e.g. glucose and galactose are C-4
epimers and glucose and mannose are C-2 epimers.
 Structure of Glucose
Glucose has two crystalline forms with slightly different
properties.
• α-D-Glucose: If D-glucose is crystallized from water, it
has a m.p. 146 oC and its specific rotation is +112.2 o;
called α-D-Glucose.

• β-D-Glucose: If D-glucose is crystallized from pyridine

or hot glacial acetic acid solution, it has a m.p. 148-150
o
C and its specific rotation is +18.7 o; called β-D-
Glucose.
 Mutarotation
• When α-D-glucose is dissolved in water, its specific rotation gradually
changes with time and reaches a stable value of +52.7 o. When β-D-
glucose is similarly treated its rotation attains the same value.

• This change is called mutarotation, is due to the formation (from

either α- or β- D-glucose) of equilibrium mixture consisting of 1/3 α-D-
glucose, 2/3 β-D-glucose and very small amount of linear form of
glucose. Thus α and β isomers are intercovertible in aqueous
solution.
Thank You