BIC 201 CARBOHYDRATE
BIC 201 CARBOHYDRATE
1
04/02/2025
MODULE 5
CHEMICAL
COMPOSITION
OF CELLS
04/02/2025 2
TOPIC 9
CARBOHYDRAT
E
04/02/2025 3
OUTLINES
Introduction
Structure
Types of carbohydrate
Functions of carbohydrate
Conclusion
INTRODUCTION
• Cells, the basic units of life, are composed of various chemical substances
that contribute to their structure, function, and survival.
• The component of cell includes;
Water
Inorganic ions: sodium, potassium, calcium, magnesium, chloride ions e.t.c
Carbohydrate
Proteins
Lipids
Nucleic acids
CARBOHYDRATES
Carbohydrate : compounds contains H, C & O
with the comp : (CH2O)n (Hydrate of carbon)
Carbohydrates : Consist of sugar (saccharum)
Sugars : compound that contains alcohol &
carbonyl functional group
Carbonyl func.group : >C=o
Adehyde aldose
Ketone ketose
Example
s:
Classification
Carbohydrate
HAWORTH STRUCTURES
An English chemist W.N. Haworth
gave a more accurate picture of
carbohydrate structure. (Ref. P.205
of textbook)
FISHER AND HAWORTH FORMS OF SUGAR
SUMMARY OF SUGAR STRUCTURES
• ISOMERS- compounds that have the same chemical formula e.g. fructose,
glucose, mannose, and galactose are isomers of each other having formula
C6H12O6.
• 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.
• ENANTIOMERS- a special type of isomerism found in pairs of structures that
are mirror images of each other. The mirror images are termed as
enantiomers and the two members are designated as D- and L- sugar. The
vast majority of sugars in humans are D-sugars.
• CYCLIZATION OF SUGARS- most monosaccharides with 5 or more carbon
atoms are predominately found in a ring form, where the aldehyde or
ketone group has reacted with an alcoholic group on the same sugar group
to form a hemiacetal or hemiketal ring.
Pyranose ring- if the ring has 5 carbons and 1 oxygen.
Furanose ring- if the ring is 5-membered (4 carbons and 1 oxygen
IMPORTANT REACTIONS IN MONOSACCHARIDES
1. Mutarotation
2. Oxidation
3. Reduction
4. Isomerization
5. Esterification
6. Glycoside formation
IMPORTANT REACTIONS IN MONOSACCHARIDES
Details
1. Mutarotation –
alfa and beta forms of sugars are readily interconverted when dissolved in water
2 Oxidation and reduction
in presence of oxidising agents, metal ions (Cu2+) and enzymes, monosacchs undergo several
oxidation reactions e.g. Oxidation of aldehyde group (R-CHO) yields aldonic acid; of terminal
CH2OH (alcohol) yields uronic acid; and of both the aldehyde and CH2OH gives aldaric acid. The
carbonyl groups in both aldonic and uronic can react with an OH group in the sam
3 REDUCTION
reduction of the aldehyde and ketone groups of monosacchs yield sugar alcohols (alditols)
Sugar alcohols e.g.sorbitol, are used commercially in processing foods and pharmaceuticals. e
molecule to form a cyclic ester lactone.
IMPORTANT REACTIONS (Cont)
4. ISOMERIZATION
Monosaccharides undergo several types of isomerization e.g. D-glucose in alkaline solution for several
hours containn D-mannose and D-fructose. The conversion of glucose to mannose is termed
epimerization. .
5 ESTERIFICATION
Free OH groups of carbohydrates react with acids to form esters. This reaction an change the physical and
chemical propteries of sugar.
6. GLYCOSIDE FORMATION-
Hemiacetals and hemiketals reaction with alcohols to form the corressponding aceta or ketal (p.210 of
Text).On the contrary when a cyclic hemiacetal or hemiketal form of monosaccharide reacts with alcohol,
the new linkage is called glycosidic linkage and the compound glycoside.
Alfa & beta GLYCOCIDIC BOND
REDUCING SUGARS
D-Glucose:
D-glucose (dextrose) is the primary fuel in living cells especially in
brain cells that have few or no mitochondria.
Cells such as eyeballs have limited oxygen supply and use large
amount of glucose to generate energy
• FRUCTOSE
• D-fructose (levulose) is often referred as fruit sugar and is found in some
vegetables and honey
• This molecule is an important member of ketose member of sugars
• It is twice as sweet as sucrose (per gram basis) and is used as sweeting agent
in processed food products
• It is present in large amounts in male reproductive tract and is synthesised in
the seminal vesicles.
Important monosaccharides.
Cont....
• GALACTOSE
• is necessary to synthesize a variety of biomolecules
(lactose-in mammalary glands, glycolipids, certain
phospholipids, proteoglycans, and glycoproteins)
• Galactose and glucose are epimers at carbon 4 and
interconversion is catalysed by enzyme epimerase.
• Medical problems – galactosemia (genetic disorder) where
enzyme to metabolize galactose is missing; accumulation of
galactose in the body can cause liver damage, cataracts,
and severe mental retardation
MONOSACCHARIDE DERVATIVES
• URONIC ACIDS – formed when terminal CH2OH group
of a mono sugar is oxidised
• Important acids in animals – D-glucuronic acid and its
epimer L-iduronic acid
• In liver cells glucuronic acid combines with steroids, certain
drugs, and bilirubin to improve water solubility thereby
helping the removal of waste products from the body
• These acids are abundant in the connective tissue
carbohydrate components.
Mono sugar derivatives
• AMINO SUGARS –
• Sugars in which a hydroxyl group (common on carbon 2) is
replaced by an amino group e.g. D-glucosamine and D-
galactosamine
• common constituents of complex carbohydrate molecule
found attached to cellular proteins and lipids
• Amino acids are often acetylated e.g. N-acetyl-
glucosamine.
Mono sugar derivatives
• DEOXYSUGARS
• monosaccharides in which an - H has replaced an – OH
group
• Important sugars: L-fucose (formed from D-mannose by
reduction reactions) and 2-deoxy-D-ribose
• L-fucose – found among carbohydrate components of
glycoproteins, such as those of the ABO blood group
determinates on the surface of red blood cells
• 2-deoxyribose is the pentose sugar component of DNA.
GLYCOSIDES
• Monosaccharides can be linked by glycosidic bonds (joining of
2 hydroxyl groups of sugars by splitting out water molecule) to
create larger structures.
• Disaccharides contain 2 monosaccharides e.g. lactose
(galactose+glucose); maltose (glucose+glucose);
sucrose (glucose+fructose)
• Oligosaccharides – 3 to 12 monosaccharides units e.g.
glycoproteins
• Polysaccharides – more than 12 monosaccharides units e.g.
glycogen (homopolysaccharide) having hundreds of sugar
units; glycosaminoglycans (heteropolysaccharides) containing a
number of different monosaccharides species.
DISACCHARIDES
AND
OLIGOSACCHARIDES
DISACCHARIDES AND
OLIGOSACCHARIDES
• Configurations: alfa or beta ( 1,4, glycosidic bonds or
linkages; other linkages 1,1; 1,2; 1,3; 1,6)
• Digestion aided by enzymes. Defficiency of any one
enzyme causes unpleasant symptoms (fermentation)
in colon produces gas [bloating of cramps].
• Most common defficiency, an ancestoral disorder,
lactose intolerance caused by reduced synthesis of
lactase
Important sugars of Disaccharides
• LACTOSE
(milk sugar) disaccharide found in milk; composed of one molecule
of galactose and glucose linked through beta(1,4) glycosidic
linkage; because of the hemiacetal group of the glucose
component, lactose is a reducing sugar
MALTOSE ( malt sugar)
An intermediate product of starch hydrolysis; it is a disaccharide with an alfa(1,4) glycosidic linkage
between two D-glucose molecules; in solution the free anomeric carbon undergoes mutarotation
resulting in an equilibrium mixture of alfa and beta – maltoses; it does not occur freely in nature
• SUCROSE
common table sugar: cane sugar or beet sugar produced in the
leaves and stems of plants; it is a disaccharide containing both
alfa-glucose and beta-fructose residues linked by
alfa,beta(1,2)glycosidic bond.
• CELLOBIOSE
degradation product of cellulose containing two molecules of glucose
linked by a beta (1,4) glycosidic bond; it does not occur freely in
nature
OLIGOSACCHARIDE SUGARS
Hyaluronic acid
Occurence : synovial fluid, ECM of loose connective tissue
Hyaluronic acid is unique among the GAGs because it does not
contain any sulfate and is not found covalently attached to proteins. It
forms non-covalently linked complexes with proteoglycans in the
ECM.
Hyaluronic acid polymers are very large (100 - 10,000 kD) and can
displace a large volume of water.
Hyaluronic acid (D-glucuronate + GlcNAc)
Dermatan sulfate (L-iduronate + GlcNAc
sulfate)
.
blocks of nucleotides)