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Medical Biochemistry and Molecular
Biology
CARBOHYDRATE CHEMISTRY
By
HusseinAbdelaziz
Disaccharides
 Disaccharides consist of two sugars joined
by an O-glycosidic bond.
 The most abundant disaccharides are
sucrose, lactose and maltose.
 Other disaccharides include isomaltose,
cellobiose and trehalose.
 The disaccharides can be classified into :
Homodisaccharides
Heterodisaccharides.
3
Polysaccharides(glycans)
 Def.: They consist of more than 10 monosaccharide units and/or their
derivatives.
 Types:
 I-Homopolysaccharides (homoglycans): If a polysaccharide
contains only one type of monosaccharide molecule.
 Examples : starch, glycogen, dextran, dextrin, cellulose and inulin.
 Also, they can be classified into:
1. Glucosan: starch , glycogen, dextran, dextrin, cellulose.
2. Fructosan : inulin
 II-Heteropolysaccharides (heteroglycans): those containing more
than one type of monosaccharides or their derivatives.
 Examples ; glycosaminoglycans, proteoglycans, glycoproteins,
agar, gum Arabic and pectin.
4
Starch
Composition: It is formed of α-D glucose units
(glucosan).
 It is the most common storage polysaccharide in
plants.
5
α -Dextrin
 Def. Products of partial hydrolysis of starch
 Composition: α -Dextrin is made up of several
glucose units joined by an α-1  4 linkage in
addition to α-1  6 linkages .
 Function: Dextrin is used as mucilage .
6
Glycogen
 Sructural unit : α-glucose units (glucosan).
 Bonds: Basic bond is α 14 & α16at the
branching point
 branches occurs every 10 glucose units
 Site and function: It is the major form of
storage polysaccharides in animals
 in liver and muscles
7
Dextran:
 It is formed of α-glucose units (glucosan).
 It is a storage polysaccharide in yeasts and bacteria.
 consists of glucose, but differs from glycogen and
starch in that they are joined mainly by α-16
linkages.
 Occasional branches are formed by α-1 2, α-1 3
or α-14 linkages depending on the species.
 Functions:
1- Support medium for column chromatography of
macromolecules
2- Replacement therapy in blood loss.
8
Cellulose
It is formed of β-D-glucose units linked together by β (1
4) glycosidic bonds.
 It is the most abundant natural polymer found in the
world.
 It is found in the cell walls of nearly all plants
 Nutritive value of Cellulose in diet:
 It is extremely resistant to hydrolysis whether by acid
or by the digestive tract amylases. So, it can stimulate
peristaltic movement and prevent constipation.
 NB: The bacteria that live in the gut of ruminant
animals secrete cellulase enzyme (β- glucosidase) which
is effective in the hydrolysis of cellulose.
9
Inulin
 It is formed of fructose (fructosan).
 It is readily soluble in warm water.
 Function:
1. Inulin clearance test to determine the rate of
glomerular filtration (Renal function test).
2. It can be used as a diet for diabetics.
10
Glycosaminoglycans (GAGs)
(Mucopolysaccharides)
 Glycosaminoglycans are long linear
(unbranched) heteropolysaccharide chains.
 Composition:composed of a repeating
disaccharide unit
 (acidic sugar-amino sugar)n.
A. The amino sugar is either D-glucosamine or
D-galactosamine in which the amino group
is usually acetylated, and sometimes sulphated.
B. The acid sugar is either glucuronic or L
iduronic .11
1-Hyaluronic acid
glucuronic acid
Composition:
Acid sugar
N-acetylglucosamineaminosugar
The only nonsulfated.
-not incorporated into proteoglycan structure.
Sulfate group
synovial fluid of joints, vitreous humor of eye, ECM of
loose connective tissue
Site
shock absorbing, lubricant.Main function
12
4-Dermatan sulate3-Keratan sulfate2-Chondriotin
sulfate
L-iduronic acidno uronic acid)glucuronic acid
Composition:
Acid sugar
N-
acetylgalactosamin
e
N-
acetylglucosamine
and galactose -6-
sulfate
N-
acetylgalactosamine
aminosugar
SulfatedSulfatedsulfatetedSulfate group
skin, blood vessels,
heart valves
cornea, bone,
cartilage
aggregated with
chondroitin
sulfates
cartilage, tendons,
ligaments, bone,
heart valves, aorta.
Site
protective &
supportive
protective &
supportive
Most abundant GAG;
protective &
supportive
Main function
13
6-Heparan sulate5-Heparin
glucuronic or iduronic acidglucuronic or iduronic acidComposition:
Acid sugar
glucosamines are acetylatedGlucosamine (non acetylated)aminosugar
Sulfated but with Fewer
sulfate groups than heparin
Sulfated in both the amino and
acid sugar component
Sulfate group
Extracellular GAG, basement
membranes, components of
cell surfaces
component of intracellular
granules of mast cells lining the
arteries of the lungs, liver and
skin
Site
Component of cell surfaceAnticoagulantMain function
14
Proteoglycans
 All of the glycosaminoglycans except
hyaluronic acid and heparin are found
covalently attached to protein, forming
proteoglycan monomers.
 A proteoglycan monomer found in cartilage
consists of a core protein to which the linear
carbohydrate chains are covalently attached.
15
Glycoproteins
 Glycoproteins are proteins to which oligosaccharides are covalently
attached.
 Functions: Membrane-bound glycoproteins participate in:
 1- Cell surface recognition (by other cells, hormones, viruses),
 2- Cell surface antigenicity (such as the blood group antigens),
 3- Components of the extracellular matrix and of the mucins of
the gastrointestinal and urogenital tracts, where they act as protective
biologic lubricants.
 4- Almost all of the globular proteins present in human plasma
(with the exception of albumin) and the secreted enzymes and
proteins are glycoproteins.
16
11/10/2014 17Ahmed A.Albadry
GREAT
THANKS
Hussein Abdelaziz

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Bio l3

  • 1.
  • 2. 2 Medical Biochemistry and Molecular Biology CARBOHYDRATE CHEMISTRY By HusseinAbdelaziz
  • 3. Disaccharides  Disaccharides consist of two sugars joined by an O-glycosidic bond.  The most abundant disaccharides are sucrose, lactose and maltose.  Other disaccharides include isomaltose, cellobiose and trehalose.  The disaccharides can be classified into : Homodisaccharides Heterodisaccharides. 3
  • 4. Polysaccharides(glycans)  Def.: They consist of more than 10 monosaccharide units and/or their derivatives.  Types:  I-Homopolysaccharides (homoglycans): If a polysaccharide contains only one type of monosaccharide molecule.  Examples : starch, glycogen, dextran, dextrin, cellulose and inulin.  Also, they can be classified into: 1. Glucosan: starch , glycogen, dextran, dextrin, cellulose. 2. Fructosan : inulin  II-Heteropolysaccharides (heteroglycans): those containing more than one type of monosaccharides or their derivatives.  Examples ; glycosaminoglycans, proteoglycans, glycoproteins, agar, gum Arabic and pectin. 4
  • 5. Starch Composition: It is formed of α-D glucose units (glucosan).  It is the most common storage polysaccharide in plants. 5
  • 6. α -Dextrin  Def. Products of partial hydrolysis of starch  Composition: α -Dextrin is made up of several glucose units joined by an α-1  4 linkage in addition to α-1  6 linkages .  Function: Dextrin is used as mucilage . 6
  • 7. Glycogen  Sructural unit : α-glucose units (glucosan).  Bonds: Basic bond is α 14 & α16at the branching point  branches occurs every 10 glucose units  Site and function: It is the major form of storage polysaccharides in animals  in liver and muscles 7
  • 8. Dextran:  It is formed of α-glucose units (glucosan).  It is a storage polysaccharide in yeasts and bacteria.  consists of glucose, but differs from glycogen and starch in that they are joined mainly by α-16 linkages.  Occasional branches are formed by α-1 2, α-1 3 or α-14 linkages depending on the species.  Functions: 1- Support medium for column chromatography of macromolecules 2- Replacement therapy in blood loss. 8
  • 9. Cellulose It is formed of β-D-glucose units linked together by β (1 4) glycosidic bonds.  It is the most abundant natural polymer found in the world.  It is found in the cell walls of nearly all plants  Nutritive value of Cellulose in diet:  It is extremely resistant to hydrolysis whether by acid or by the digestive tract amylases. So, it can stimulate peristaltic movement and prevent constipation.  NB: The bacteria that live in the gut of ruminant animals secrete cellulase enzyme (β- glucosidase) which is effective in the hydrolysis of cellulose. 9
  • 10. Inulin  It is formed of fructose (fructosan).  It is readily soluble in warm water.  Function: 1. Inulin clearance test to determine the rate of glomerular filtration (Renal function test). 2. It can be used as a diet for diabetics. 10
  • 11. Glycosaminoglycans (GAGs) (Mucopolysaccharides)  Glycosaminoglycans are long linear (unbranched) heteropolysaccharide chains.  Composition:composed of a repeating disaccharide unit  (acidic sugar-amino sugar)n. A. The amino sugar is either D-glucosamine or D-galactosamine in which the amino group is usually acetylated, and sometimes sulphated. B. The acid sugar is either glucuronic or L iduronic .11
  • 12. 1-Hyaluronic acid glucuronic acid Composition: Acid sugar N-acetylglucosamineaminosugar The only nonsulfated. -not incorporated into proteoglycan structure. Sulfate group synovial fluid of joints, vitreous humor of eye, ECM of loose connective tissue Site shock absorbing, lubricant.Main function 12
  • 13. 4-Dermatan sulate3-Keratan sulfate2-Chondriotin sulfate L-iduronic acidno uronic acid)glucuronic acid Composition: Acid sugar N- acetylgalactosamin e N- acetylglucosamine and galactose -6- sulfate N- acetylgalactosamine aminosugar SulfatedSulfatedsulfatetedSulfate group skin, blood vessels, heart valves cornea, bone, cartilage aggregated with chondroitin sulfates cartilage, tendons, ligaments, bone, heart valves, aorta. Site protective & supportive protective & supportive Most abundant GAG; protective & supportive Main function 13
  • 14. 6-Heparan sulate5-Heparin glucuronic or iduronic acidglucuronic or iduronic acidComposition: Acid sugar glucosamines are acetylatedGlucosamine (non acetylated)aminosugar Sulfated but with Fewer sulfate groups than heparin Sulfated in both the amino and acid sugar component Sulfate group Extracellular GAG, basement membranes, components of cell surfaces component of intracellular granules of mast cells lining the arteries of the lungs, liver and skin Site Component of cell surfaceAnticoagulantMain function 14
  • 15. Proteoglycans  All of the glycosaminoglycans except hyaluronic acid and heparin are found covalently attached to protein, forming proteoglycan monomers.  A proteoglycan monomer found in cartilage consists of a core protein to which the linear carbohydrate chains are covalently attached. 15
  • 16. Glycoproteins  Glycoproteins are proteins to which oligosaccharides are covalently attached.  Functions: Membrane-bound glycoproteins participate in:  1- Cell surface recognition (by other cells, hormones, viruses),  2- Cell surface antigenicity (such as the blood group antigens),  3- Components of the extracellular matrix and of the mucins of the gastrointestinal and urogenital tracts, where they act as protective biologic lubricants.  4- Almost all of the globular proteins present in human plasma (with the exception of albumin) and the secreted enzymes and proteins are glycoproteins. 16