CARBOHYDRATES

DR. SAID M. R. KEWEDAR

 LECTURE OUTLINE
 The Importance of carbohydrates.

 The Definition of Carbohydrates.

 The Classification of Carbohydrates.

 The Difference between various

Isomers..
 CARBOHYDRATE: IMPORTANCE
 Most Abundant Class of
Biomolecules.
 An Important Macronutrient.
 Performs important physiological
functions in the body.
 Associated with Pathological
Conditions (Diabetes Mellitus,
Lactose Intolerance).
DEFINING CARBOHYDRATES

Carbohydrates or Saccharides
(Greek Sakcharon meaning "Sugar")
 Organic compounds composed of
Carbon, Hydrogen and oxygen.

 Many Carbohydrates also contain

Nitrogen and other elements.
 Carbohydrates derive their name
from a Misleading Concept
'Hydrates of Carbon’
 Hydrogen and Oxygen in Carbohydrates
were found to be present in the same
proportion as in water. (2:1).(E.g.
Glucose C6H12O6 or C6 (H2O)6).

 It
is due to this fact that compounds
derived their name “Carbon Hydrate”.
GLUCOSE
H-C=O

H-C-OH

OH-C-H

H-C-OH

H-C-OH

CH2OH
This term is not a perfect derivation
as many carbohydrates do not have
the same proportion as water.

Example: DEOXYRIBOSE (C5H10O4)

H-C=O

H-C-H

H-C-OH

H-C-OH

CH2OH
CHEMICAL DEFINITION OF
CARBOHYDRATES
 Polyhydroxyl:
Having more than one
hydroxyl group.
(-OH)

 Functional Group: It is a specific

group of atoms or bonds which are
part of a larger hydrocarbon
chain.(Provide a specific chemical
behaviour).
 For carbohydrates, the functional group is
the carbonyl group which may be either

Aldehyde Group (H-C=O)

Or
Keto Group (C=O)
WHAT IS SIMILAR & DIFFERENT
IN THESE TWO STRUCTURES?
H-C=O CH2OH
 
H-C-OH C=O
 one hydroxylgroup in both
More than
OH-C-H OH-C-H
 
H-C-OH H-C-OH
 
CH2OH CH2OH
WHAT IS COMMON & DIFFERENT
IN THESE TWO STRUCTURES?
H-C=O CH2OH
 
H-C-OH C=O

Carbonyl Group inboth But?
OH-C-H OH-C-H
 
H-C-OH H-C-OH
 
CH2OH CH2OH
WHAT IS COMMON & DIFFERENT
IN THESE TWO STRUCTURES?
H-C=O CH2OH
 
H-C-OH C=O

Aldehyde 
in 1 and Ketone in 2
OH-C-H OH-C-H
 
H-C-OH H-C-OH
 
CH2OH CH2OH
 Carbohydrates are
Polyhydroxy Alcohols
with Carbonyl groups
Which May Either Be
Aldehyde (H-C=O) or
Keto (C=O) Groups.
 H-C CH2OH
CAN YOU  O 
VISUALIZE H-C-OH C
EITHER  
ALDEHYDE OH-C-H OH-C-H
OR  
KETONE H-C-OH H-C-OH
GROUP IN  
THIS H-C-OH H-C-OH
POLYHYDROX  
Y ALCOHOL? CH2OH CH2OH
 H-C CH2OH

HOH 
NO! BUT O
HYDROLYSIS H-C-OH C
OF THIS  
COMPOUND OH-C-H OH-C-H
YIELDS TWO  
COMPOUNDS H-C-OH H-C-OH
WITH  
ALDEHYDE H-C-OH H-C-OH
OR KETONE  
GROUPS CH2OH CH2OH
 H-C =O CH2OH

HOH 
NO! BUT O
HYDROLYSIS H-C-OH O=C
OF THIS  
COMPOUND OH-C-H OH-C-H
YIELDS TWO  
COMPOUNDS H-C-OH H-C-OH
WITH  
ALDEHYDE H-C-OH H-C-OH
OR KETONE  
GROUPS CH2OH CH2OH
MANY POLYHYDROXY ALCOHOLS MAY
NOT HAVE AN ACTIVE ALDEHYDE OR
KETONE GROUP BUT THEY MAY YIELD
THEM ON HYDROLYSIS. THEY
ARE ALSO DESIGNATED AS
CARBOHYDRATES.
 THEREFORE, THE COMPLETE
DEFINITION OF CARBOHDRATES IS:

CARBOHYDRATES ARE
POLYHYDROXYL ALCOHOLS
WITH POTENTIALLY ACTIVE
CARBONY GROUPS WHICH MAY
BE EITHER AN ALDEHYDE OR
KETONE GROUP. THEY ALSO
CONTAIN THOSE COMPOUNDS,
WHICH YIELD THEM ON
HYDROLYSIS.
CLASSIFICATION OF CARBOHYDRATES
Carbohydrates are mainly classified
into four different groups:

 Monosachharides

 Disaccharides

 Oligosaccharides

 Polysaccharides
 MONOSACCHARIDES

 Monosaccharides are those carbohydrates

which Cannot be Hydrolyzed further into

more simple carbohydrates.
 Thus, they are the Simplest form of
Carbohydrates.
 Familiar examples are:
Glucose, Fructose, Ribose & Galactose.
MONOSACCHARIDES ARE FURTHER
CLASSIFIED ON THE BASIS OF:

 Aldehyde or Ketone Group:

Aldomonosaccharides (Aldoses).

Ketomonosaccharides (Ketoses).

 Carbon Chain Length.

Trioses.

Tetroses.

Pentoses.

Hexoses.

Heptoses.
 CARBONYL GROUP
H-C=O CH2OH
 
H-C-OH C=O
 
OH-C-H GLUCOSE OH-C-H
 
H-C-OH FRUCTOSE--> H-C-OH
 
H-C-OH H-C-OH
 
CH2OH CH2OH
 CARBON CHAIN
H-C=O
 H-C=O
H-C-OH 
 OH-C-H
OH-C-H 
GLUCOSE H-C-OH

H-C-OH ARABINOSE--> 
 H-C-OH
H-C-OH 
 CH2OH
CH2OH
 EXAMPLES OF
MONOSACCHARIDES
NO. OF CARBON ALDO KETO
ATOMS

3C TRIOSE GLYCERALDEHYD DIHYDROXYACET

E ONE

4C TETROSE ERYTHROSE ERYTHRULOSE

5C PENTOSE RIBOSE, XYLOSE RIBULOSE,

XYLULLOSE

6C HEXOSE GLUCOSE, FRUCTOSE

GALACTOSE,
MANNOSE
GLYCERALDEHYDE
 GLYCERALDEHYDE IS THE SIMPLEST
MONOSACCHARIDE(PARTICULARLY
ALDOSES)

 IT CANNOT BE HYDROLYZED FURTHER.

 IT IS THE SMALLEST
POSSIBLESTRUCTURE THAT IS A
CARBOHYDRATE CANNOT HAVE LESS
THAN 3 CARBON ATOMS.

 GENERAL FORMULA OF
MONOSACCHARIDE: (C•H2O)N
(WHERE N IS ANY NUMBER OF THREE OR
GREATER)
 ISOMERISM
 Isomers are basically molecules that
have the same chemical formula but
they differ in their chemical
structures.

 AsymmetricCarbon is an important
determinant of Isomerism.

 Asymmetric Carbon is that Carbon

which is attached with four different
groups.
STRAIGHT CHAIN STRUCTURE OF TYPICAL
MONOSACCHARIDE (GLUCOSE)
Anomeric
Carbon

Epimeric
Carbons

Penultimate
Carbon
Terminal
Alcohol Carbon
THE ASSIGNMENT OF D OR L IS MADE ACCORDING
TO THE ORIENTATION OF THE PENULTIMATE
CARBON

If the Hydroxyl Group is on the right

the molecule is a D sugar,
Otherwise It is an L sugar.

OH H L-Sugar : D-Sugar
D AND L ISOMERISM PRODUCE MIRROR
IMAGES
 EPIMERISM
 Isomers which differ from each other
only with regard to oh group on a
single asymmetric carbon atom.
 OPTICAL ISOMERS

 When a beam of polarized light is

passed through sugars, they will be
rotated either towards right or left.

 RightRotation (dextrorotatory) E.g.

D- Glucose

 Left
Rotation (levorotatory) E.g. D-
Fructose
 MONOSACCHARIDE DERIVATIVES OF
BIOLOGICAL IMPORTANCE
 Oxidation Products (Sugar Acids)

 Reduction Products (Sugar Alcohols).

 Amino Sugars.

 Sugar Phosphates.
 OXIDATION PRODUCTS (SUGAR ACIDS)
 When oxidized under proper conditions,
Aldoses may form three types of acids
(Sugar Acids):

 Uronic Acids.

 Aldonic acids.

 Saccharic Acids.

 Type of sugar Acid produced depends on

which carbon is oxidized.
 H-C=O

H-C-OH URONIC ACID

OH-C-H Oxidation Of Aldose
 At Primary Alcohol
H-C-OH (Terminal Carbon)

H-C-OH

COOH
CH2OH
 H-C=O
COOH ALDONIC ACID

H-C-OH Oxidation Of Aldose
 At
OH-C-H Carbonyl Carbon
 (Aldehyde Group)
H-C-OH

H-C-OH

CH2OH
 COOH
H-C=O

H-C-OH Saccharic Acid

OH-C-H Oxidation Of Aldose
 At Both Aldehyde &
H-C-OH Terminal Carbons

H-C-OH

CH2OH
COOH
EXAMPLES OF ALDOSES WITH THEIR
CORRESPONDING URONIC ACIDS ARE:

Sugar Uronic Acids

Glucose Glucuronic acid,

Iduronic acid
------------- ----------------------
Mannose Mannuronic acid
------------- ----------------------
Galactose Galacturonic acid
------------- ------------------------
EXAMPLES OF ALDOSES WITH THEIR
CORRESPONDING ALDONIC ACIDS ARE:
Sugar Aldonic Acids

Glucose Gluconic acid

------------- ----------------------
Mannose Mannonic acid
------------- ----------------------
Galactose Galactonic acid
------------- ------------------------
Amino Sugar: Substitution of
Amino Group for a
H-C=O
 Hydroxyl Group of a
H-C-OH
NH2 Sugar Results in the
 Formation of an
OH-C-H
 Amino Sugar.
H-C-OH The Amino Group
 is attached to
H-C-OH
 Carbon 2.
CH2OH
COMMON EXAMPLES OF AMINO SUGARS
(AMINOSACCHARIDES)
 Galactosamine

 Glucosamine
SUGAR ALCOHOLS; REDUCTION PRODUCTS
 SugarAlcohols are obtained by reduction
of Monosaccharides (Both Aldoses and
Ketoses) and disaccharides.
 Sugaralcohols, also known as Polyols,
Polyhydric Alcohols, or Polyalcohols.
SUGAR ALCOHOLS ARE THE HYDROGENATED
FORMS OF THE ALDOSES OR KETOSES
H- C=O + H2 CH2OH
 
H-C-OH H-C-OH
 
OH-C-H OH-C-H
 
H-C-OH H-C-OH
 
H-C-OH H-C-OH
 
CH2OH CH2OH
Glucose Sorbitol
Sugars with their Corresponding Alcohols
Glyceraldehyde & Glycerol
Dihydroxyacetone
Glucose Sorbitol (Glucitol)
Mannose Mannitol
Fructose Sorbitol & Mannitol
Galactose Dulcitol
Ribose Ribitol
Erythrose Erythritol
Xylose Xylitol
Lactose Lactitol
Maltose Maltitol
 Sugar Phosphates
Phosphate Esters formed by various
Monosaccharides are of Great Importance
in Metabolic Reactions.
Sugar phosphates of biological importance.
Ribose and Deoxyribose in Nucleic Acids
are Phosphate Esters of these
monosaccharides.
Phosphates of Glucose, Fructose and
Glyceraldehyde etc. are important
intermediate compounds in carbohydrate
metabolism of almost all the cells.
 DISACCHARIDES
Two Joined Monosaccharides.
Sucrose: Glucose + Fructose
Maltose: Glucose + Glucose
Lactose: Glucose + Galactose
OLIGOSACCHARIDES

Composed Of:

 Three To Ten Monosaccharide

Units.

 E.g. Fructooligosaccharides
POLYSACCHARIDES

Larger Than Ten Monosaccharide

Units.
Can Reach Many Thousands Of Units.
 Homopolysaccharides.

 Heteropolysaccharides.
 HOMOPOLYSACCHARIDES

 Similar Types of Monosaccharide

Units.

Starch

Glycogen

Cellulose
 HETEROPOLYSACCHARIDES

Different Types of Monosaccharide


Units.
Mucopolysaccharides


(Glycosaminoglycans that contain

galactose and amine sugars)
Agar (Contains various sugars like


Glucose, Galactose)