Concept 　 of biochemistry

Carbohydrates

Arman Wijonarko
Dept. of Entomology and Plant Pathology
 Objectives

Define what a carbohydrate molecule is

Recognise and classify carbohydrate molecules
Explain why carbohydrates are important
Name other molecules that interact with
carbohydrates and explain how and why these
interactions occur
 Lecture Outline

 Monosaccharides  Dissaccharides &

Definition Energy storage
Nomenclature  Glycosidic bond
Fischer projections  Glycolysis
Monosaccharides  Complex
Haworth projections Carbohydrates &
Furanose & Pyranose Function
rings  Starch & glycogen
Modified Sugars  Cellulose
Sugars in Nucleic Acids  Blood groups
 Glycoproteins
Why Carbohydrates ?
Carbohydrates

Structure and functions

 Caloric intake for most animal life,

microorganism
 Central in photosynthetic process

 Storage place (starch and glycogen)

 Other functions
Other function
 Structure and supportive element of cell
wall of bacteria and plants
 Cell coat
 Lubricate skeletal joints
 Adhesion between cell
 Biological specificity on cell surface
Functions
• Carbohydrates serve as:
From: Elliott WH & Elliott DC. (1997) Biochemistry and
Molecular Biology. New York: Oxford University Press. p170

– Energy stores
• Liver and muscle glycogen
– Fuels
• Catabolised in glycolysis to produce
ATP
– Structural molecules Adapted from: Bettelheim FA and March J (1990)
Introduction to Organic and Biochemistry

• eg. Ribose forms part of structure of ATP

(International Edition). Philadelphia: Saunders
College Publishing p383.
and nucleic acids (DNA and RNA)
• Molecules on surface of cell membranes
involved in:
– Cell recognition
– Cell adherence
– Hydrophilic properties attract water layer From: Tortora GJ & Grabowski SR (2000) Principles of
as lubricant Anatomy and Physiology (9th Edition). New York: John Wiley
& Sons, p62
Structures
• Carbohydrates exist as:
– Monosaccharides
• Single structure which can contain up to 8
carbon atoms
• Not degraded by hydrolysis
– Disaccharides
• Two monosaccharides bonded together
– Polysaccharides
• More than two monosaccharides bonded
together
What is a Carbohydrate?
Aldehyde or ketone compounds with multiple
hydroxyl groups (OH)
Ketones – both groups attached to carbonyl
group are carbon
Aldehydes – one carbon and one hydrogen
attached to carbonyl group

Acetone: Acetaldehyde
What is a Carbohydrate?
Simplest carbohydrate molecule is a
monosaccharide : (C-H20)n : carbon h
ydrate
Monosaccharides have 3 to 7
carbons
Either aldehyde or ketone group and
hydroxyl (OH) groups on nearly
every carbon
Polyhydroxyaldehydes or
Polyhydroxyketones
Polyhydroxyaldehydes

Galactose Glucose
Ribose

R
Polyhydroxyketone

R R
 Hexose: aldo & keto

R
R R
Monosaccarides
 Monosaccharide Nomenclature

C Ketone Aldehyde Examples

4 Tetrose Tetrulose Erythrose,Threose

5 Pentose Pentulose Ribulose,Ribose

6 Hexose Hexulose Fructose,Glucose

7 Heptose Heptulose Sedoheptose, Sedoheptulose

Which classification fits this sugar?
Which classification fits this sugar?
Stereochemistry
 Stereochemistry – study of arrangement of
atoms in 3D space
 Carbohydrates with identical functional
groups linked in the same order but with
different spatial orientation
 Identical molecules can be made to
superimpose by rotating and flipping
 Different compounds cannot be made to
superimpose
Are these compounds the same?
Chiral Carbon Atom
Single asymmetric carbon
Fischer Projections

 Using these rules the

distinguishing features of the 3D
structure of stereoisomers can
easily and accurately represented
with 2D drawings
 Fischer projection named after
Emil Fischer who established the
molecular structures of many
sugars
 TRIOSE

Glyceraldehyde has 1 asymmetric carbon atom

(2n = 21) therefore there are two stereoisomer
s.

D & L -glyceraldehyde are enantiomers, or

mirror images of each other.
 Anomers or Anomeric Carbon
 Two stereoisomers ( designated as  and )
of a given sugar that differ only in the config
uration about the carbonyl (anomeric) carbo
n atom.
 the -isomer has the hydrogen atom above the
plane of the ring in the Haworth projection (=h
ydrogen below).
Haworth Projections
Summary
 Why are carbohydrates important?
 Primary energy store
 Structural properties
 Antigenic properties
 What is a carbohydrate?
 Aldehyde or ketone compounds with multiple hydroxyl groups
(OH)
 Stereochemistry
 Carbohydrates have identical functional groups linked in the
same order but with different spatial orientation
 Enantiomers
 Drawing sugars
 Fischer projections
 Stereo chemistry
Disaccharide