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BIO 211

LECTURE 5

BIOMOLECULES:
CARBOHYDRATES

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Lecture objectives
 Students should be able to describe/explain

 Classes of Carbohydrates

 Structure and function of carbohydrates

 Carbohydrates involvement in surfaces

 Carbohydrates and metabolic diseases

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Overview

 Carbohydrates (Saccharides) are the most abundant


organic molecules in nature.
 Have a wide range of functions:
 Dietary calories for most organisms
 Storage form of energy
 Cell membrane components & mediate in intercellular
communications.
 Structural components of many organisms; cell walls of
bacteria, exoskeleton of insects, fibrous cellulose of plants.
 Empirical formula for many simpler carbohydrates is
(CH2O)n, where n≥3.
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overview

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Classification & Structure
 Monosaccharides (simple sugars) can be classified
according to the number of carbon atoms they contain:
 examples found in humans are given in table.

Generic Name Examples

3 Carbons Trioses Glyceraldehyde

4 Carbons Tetroses Erythroses

5 Carbons Pentoses Ribose

6 carbons Hexoses Glucose

7 carbons heptoses sedoheptulose

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Classification & Structure
 Monossacharides can also be classified according to the
type of carbonyl group they contain
 Those with an aldehyde as their carbonyl group are called
aldoses, whereas those with a keto as their carbonyl group
are called ketoses.
 E.g.

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Classification & structure

 Carbohydrates with a free carbonyl group have the


suffix –ose.
 Monosaccharides can be linked by a Glycosidic bonds
to create larger structures.

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Carbohydrates Structures
Disaccharides, oligosaccharides, polysaccharides
 Disaccharides contain two monosaccharide units
 Oligosaccharides contain 3 to 10 monosaccharide
units,
 Polysaccharides contain more than 10
monosaccharides units, can be hundreds.

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Carbohydrates Structures
Disaccharides, oligosaccharides, polysaccharides
 Examples of disaccharides;
 Glucose + glucose = maltose
 Glucose + fructose = sucrose
 Glucose + galactose = Lactose
 Important polysaccharides include branched GLYCOGEN
(from animal sources) and STARCH and unbranched
CELLULOSE (from plant sources).
 Each is a polymer of Glucose linked by glycosidic bonds
which are formed by the enzyme glycosyltransferases.

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Classification & Structure:
isomers and epimers
 Isomers: compounds with
same chemical formula
but different structures,
e.g. fructose, glucose,
mannose, galactose are
isomers of each other.
C6H12O6
 Epimers: carbohydrates
isomers that differ in
configuration around only
one specific carbon atom
(exception of the carbonyl
carbon) e.g. glucose and
galactose are C-4 epimers

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Classification & Structure
Enantiomers
 Enantiomers: special
isomers that are mirror
images of each other.
 The two members are
designated D- and L- sugars.
(D=right and L=left)
 Majority of sugars in
humans are D- sugars.

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Classification & Structure:
cyclization of monosaccharides
 Note: its D-glucose
because of –OH on
Carbon-5 is on the right!
 Subsequent structures
resulting from this will
therefore bear the D-
glucose

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Classification & Structure:
cyclization of monosaccharides
•Only less than 1% of monosaccharides with five or more
carbons exists in the open-chain (Acyclic) form in solution.
•Majority are in the Ring (cyclic) form in which the
aldehyde (or keto) group has reacted with an alcohol group
of the same sugar.

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Structure & Characteristics

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COMPLEX CARBOHYDRATES

 Carbohydrates can be attached by glycosidic bonds to


noncarbohydrate structures including purine and
pyrimidine bases, aromatic rings, proteins (glycoproteins),
and lipids (glycolipids) to form GLYCOSIDES.
 If the noncarbohydrate group on which the sugar is linked
is an -NH2 group the structure is an N-glycoside; the bond
is N-glycosidic link
 If the group is –OH, the structure is an O-glycoside; the
bond is a O-glycosidic link.
 NOTE: All Sugar-Sugar glycosidic bonds are O-glycosidic
linkages

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CARBOHYDRATES & SURFACES

• Carbohydrate Chains, or glycolipids, glycoproteins, are


chains found on the surface of the cell membrane that
are made of carbohydrates + lipid (or) protein.

 The primary function


of these chains is to
recognize harmful cells
(cell-cell recognition)

Participation of cell surface carbohydrates


in recognition events with another cell (A),
toxins (B), viruses (C), antibodies (D) and
bacteria (E).
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CARBOHYDRATES & SURFACES

• Sugar-specific receptors (lectins) are also present


on cells and can interact with sugars on opposing
cells.

 This may result in


the adhesion of the
two cells via
carbohydrates and
specific cell-surface
Participation of cell surface carbohydrates
receptors. in recognition events with another cell (A),
toxins (B), viruses (C), antibodies (D) and
bacteria (E).
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CARBOHYDRATES & SURFACES

• carbohydrate-directed cell adhesion appears to


be important in many intercellular activities.
 E.g. infection by
bacteria and viruses
 communication
among cells of lower
eukaryotes
 specific binding of
sperm to egg;
 recirculation of Participation of cell surface carbohydrates
lymphocytes etc in recognition events with another cell (A),
toxins (B), viruses (C), antibodies (D) and
bacteria (E).
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Carbohydrates & surfaces

 Peptidoglycans:
 found on bacteria cell wall.
 Much more on Gram-
positive bacteria
 Penicillin kills bacteria by
inhibiting biosynthesis of
the cell wall

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Carbohydrate metabolic disorders
 The most common disorders are acquired or secondary
derangements in carbohydrate metabolism
 E.g.diabetic ketoacidosis, hyperosmolar coma, and
hypoglycemia, all affect the central nervous system
 Galactose and fructose disorders
 Galactosemia usually is caused by a defective component
of the second major step in the metabolism of the sugar
galactose.
 Glycogen storage disorders
 The brain, red blood cells, and inner portion of
the adrenal gland (adrenal medulla) depend on a
constant supply of glucose for their metabolic functions.

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summary

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