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Structure and Function of Carbohydrates

This document discusses the structure and function of carbohydrates. It begins with an overview of carbohydrates, noting they are the most abundant organic molecules in nature and provide energy. It then covers the classification of carbohydrates including monosaccharides, disaccharides, and polysaccharides. Specific monosaccharides like glucose and fructose are examined in depth. The document also discusses glycosaminoglycans, important heteropolysaccharides that are major components of connective tissue and provide resilience.

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Ali Seena
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93 views

Structure and Function of Carbohydrates

This document discusses the structure and function of carbohydrates. It begins with an overview of carbohydrates, noting they are the most abundant organic molecules in nature and provide energy. It then covers the classification of carbohydrates including monosaccharides, disaccharides, and polysaccharides. Specific monosaccharides like glucose and fructose are examined in depth. The document also discusses glycosaminoglycans, important heteropolysaccharides that are major components of connective tissue and provide resilience.

Uploaded by

Ali Seena
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd
You are on page 1/ 27

CARBOHYDRATES:

STRUCTURE AND
FUNCTION

By
Dr. Aliseena yussufpur
Objectives
To understand:
 The structure of carbohydrates of
physiological significance
 The main role of carbohydrates in
providing and storing of energy
 The structure and function of
glycosaminoglycans
OVERVIEW

Carbohydrates:
The most abundant organic molecules in nature
The empiric formula is (CH2O)n, “hydrates of
carbon”
Carbohydrates:
provide important part of energy in diet
Act as the storage form of energy in the body
are structural component of cell membranes
OVERVIEW CONT’D

 Many diseases associated with disorders


of carbohydrate metabolism including:
Diabetes mellitus
Galactosemia
Glycogen storage diseases
Lactose intolerance
CLASSIFICATION

 Monosaccharides: Simple sugar


 Disaccharides: 2 monosaccharide units
 Oligosaccharides: 3-10 monosaccharide units
 Polysaccharides: more than 10 sugar units
Homopolysaccharides & heteropolysaccharides
Monosaccharides
Further classified based on:

1. No. of carbon atoms

2. Functional sugar group:


Aldehyde group –
aldoses
Keto group – ketoses
Monosaccharides CONT’D

Aldose Ketose
Triose Glyceraldehyde Dihydroxyacetone
Pentose Ribose Ribulose
Hexose Glucose Fructose
Isomerism
 Isomers
Compounds having
same chemical
formula but different
structural formula
Aldo-Keto Isomers

Example:
Glucose (Aldose)
and
Fructose (Ketose)
Epimers
Epimers
CHO dimers that differ in
configuration around only
one specific carbon atom
-Glucose and galactose, C4
-Glucose and Mannose, C2

Galactose and mannose are


not epimers
Enantiomers (D- and L-Forms)

Structures that are mirror


images of each other and
are designated as D- and
L- sugars based on the
position of –OH grp on
the asymmetric carbon
farthest from the
carbonyl carbon

Majority of sugars in
humans are D-sugars
α- and β-Forms
1
CHO

H C OH
2
HO C H D-glucose

Cyclization of Monosaccharides
3
 H C OH (linear form)
4

Monosaccharides with 5 or more


H C OH
5
CH2OH
6

carbon are predominantly found in 6 CH2OH


5 O
6 CH2OH
5 O
H H H OH

the ring form 4


H
OH H 1 4
H
OH H 1

OH OH OH H
3 2 3 2
H OH H OH

-The aldehyde or ketone grp reacts with -D-glucose -D-glucose

the –OH grp on the same sugar 1


CH2OH

2C O

HO C H
-Cyclization creates an anomeric carbon 3 HOH2C 6 O 1 CH2OH
H C OH
(former carbonyl carbon) generating the H
4

C OH
5

H
H
4
HO
3
2

OH
α and β configurations
5
OH H
6
CH2OH

D-fructose (linear) -D-fructofuranose


Mutarotation

In solution, the cyclic α and β anomers of a


sugar are in equilibrium with each other, and
can be interconverted spontaneously

Fischer Projection
Fischer Projection Haworth Projection
Sugar Isomers

1. Aldo-keto

2. Epimers

3. D- and L-Forms

4. α- and β-anomers
Disaccharides

 Joining of 2 monosaccharides
by O-glycosidic bond:
Maltose (α-1, 4)= glucose + glucose

Sucrose (α-1,2) = glucose + fructose

Lactose (β-1,4) = glucose + galactose


Disaccharides CONT’D

Lactose
Polysaccharides

 Homopolysaccharides:
Branched:
Glycogen and starch (α-glycosidic polymer)
Unbranched:
Cellulose (β-glycosidic polymer)
 Heteropolysaccharides:
e.g., glycosaminoglycans (GAGs)
Reducing Sugars

 If the O on the anomeric C of a sugar is not


attached to any other structure (Free), that sugar
can act as a reducing agent

 Reducing sugars reduce chromogenic agents like


Benedict’s reagent or Fehling’s solution to give a
colored precipitate

 Urine is tested for the presence of reducing sugars


using these colorimetric tests
Reducing Sugars CONT’D

 Examples:
Monosaccharides
Maltose and Lactose

Sucrose is non-reducing, Why?


Complex Carbohydrates

 Carbohydrates attached to non-


carbohydrate structures by glycosidic bonds
(O- or N-type) e.g.,

1. Purine and pyrimidine bases in nucleic acids


2. Bilirubin
3. Proteins in glycoproteins and proteoglycans
4. Lipids found in glycolipids
Glycosidic Bonds

 N-Glycosidic

 O-Glycosidic
Glycosaminoglycans (GAGs)
 Glycosaminoglycans (GAGs) are large complexes of
negatively charged heteropolysaccharide chains
 are associated with a small amount of protein, forming
proteoglycans, which consist of over 95 percent
carbohydrate
 bind with large amounts of water, producing the gel-like
matrix that forms body's ground substance
 The viscous, lubricating properties of mucous secretions
also result from GAGs, which led to the original naming
of these compounds as mucopolysaccharides
Glycosaminoglycans (GAGs)
 GAGs are linear polymers of repeating
disaccharide units
[acidic sugar-amino sugar]n

 The amino sugar (usually sulfated) is either


D-glucosamine or D-galactosamine

 The acidic sugar is either


D-glucuronic acid or L-iduronic acid

 GAGs are strongly negatively-charged:


carboxyl groups of acidic sugars
Sulfate groups
Resilience of GAGs
Relationship between glycosaminoglycan structure and
function
 Because of negative charges, the GAG chains tend to be
extended in solution and repel each other and when
brought together, they "slip" past each other
This produces the "slippery" consistency of mucous
secretions and synovial fluid
 When a solution of GAGs is compressed, the water is
"squeezed out" and the GAGs are forced to occupy a
smaller volume. When the compression is released, the
GAGs spring back to their original, hydrated volume
because of the repulsion of their negative charges
This property contributes to the resilience of synovial
fluid and the vitreous humor of the eye
Members of GAGs
Examples of GAGs are:

1. Chondroitin sulfates: Most abundant GAG

2. Keratan sulfates: Most heterogeneous GAGs

3. Hyaluronic acid: Compared to other GAGs, it is


unsulfated and not covalently attached to protein

4. Heparin: Unlike other GAGs, Unlike other GAGs


that are extracellular, heparin is intracellular and
serves as an anticoagulant
Take home Message
Structure and function of carbohydrates
 Mono-, Di-, and Poly-saccharides
 Sugar Isomers: Aldo-keto, epimers, D- and L-, α-
and β-anomers
 Complex carbohydrates:
e.g., Glycosaminoglycans and proteoglycans
 Structure and function of GAGs
 Examples of GAGs: chondroitin sulfate, keratin
sulfate, hyaluronic acid and heparin
Reference
 Lippincott’s Illustrated reviews- Biochemistry, 6 th
Edition, pages- 83-86 and 157-159

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