BIOPHILIC
Carbohydrates
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‫الصيغ الكيميائية للفهم فقط‬
‫‪Ketoses‬‬
‫‪Aldoses‬‬
‫‪Dihydroxyacetone‬‬
‫‪Glyceraldehyde‬‬
‫يحتوي علي ‪ 3‬ذرات كربون والمجموعة الفعالة ‪ketone‬‬
‫يحتوي علي ‪ 3‬ذرات كربون والمجموعة الفعالة ‪aldehyde‬‬
‫‪Erythroulose‬‬
‫‪Erythrose‬‬
‫يحتوي علي ‪ 4‬ذرات كربون والمجموعة الفعالة ‪ketone‬‬
‫يحتوي علي ‪ 4‬ذرات كربون والمجموعة الفعالة ‪aldehyde‬‬
‫‪Trios‬‬
‫‪Tetrose‬‬
‫‪Pentose‬‬
‫‪Xyloulose‬‬
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‫‪Ribulose‬‬
‫‪Xylose‬‬
‫‪Ribose‬‬
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Aldoses
Ketoses
Hexoses
Mannose
Glucose
Galactose
Fructose
Heptoses
Heptose
Sedoheptulose
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Physical Properities Of Monosaccharides
1) Asymmetrical carbon atom (chiral carbon)
• It is the carbon atom that attatched to four different chemical gro ups
• All momosaccharides contain assymetrical carbon atom except dihydroxyacetone
2) isomers )‫(النظائر‬
 Def: compounds with the same chemical groups (Molecular weight) but differ in
arrangment of these groups (physical and chemical properities)
(due to prscence of asymmetrical carbon atom)
 Types:
a) D & L isomers (configuration)
• There are 2 forms of monosaccharides according to the attachment of OH group of the
subterminal carbon ‫االخية‬
‫الكربونة قبل‬
‫ر‬
a) If the OH is attatched to the right side → the sugar is called D
b) If the OH is attatched to the left side → the sugar is called L
• The difference make the 2 forms (D & L) mirror image to each other.
• Almost all naturally occurring carbohydrates are of D configuration
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b) Functional group isomers
• These isomers have the same carbon skeleton and the same position of groups but
differ in functional active groups (aldehyde or ketone)
• e.g: glucose and fructose
c) Epimers
• They are isomers which differ in distribution of OH groups around a single assymmetric
carbon atom other than the anomeric and the subterminal
• Glucose is an epimer to mannose at C 2
• Glucose is an epimer to galactose at C 4
• But mannose and galactose are not epimers.
Mannose
Glucose
Galactose
d) Anomers
• They are isomers different in distribution of OH group around the asymmetric
anomeric carbon atom ( C1 in aldoses & C2 In ketoses ) in ring form e.g: α glucose
and β glucose
• N.B. α and β are convertible to each other (mutarotation)
• N.B. equilibrium of solution occurs when it contains 66% β and 33% α and 1 % in
open chain
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‫‪Ring formation‬‬
‫‪Ibrahim’s Law‬‬
‫‪ )1‬يتم نقل ال ‪ OH‬الموجودة في الكربونة رقم ‪ 5‬الي المجموعة الفعالة‬
‫‪ )2‬يتم كسر الرابطة المزدوجة الموجودة في المجموعة الفعالة‬
‫‪ )3‬يتم تكوين رابطة بين ال ‪ O‬الموجودة في الكربونة الفعالة والكربونة رقم ‪5‬‬
‫‪ )4‬اي حاجة كانت موجودة علي الشمال تطلع فوق‬
‫‪ )5‬اي حاجة كانت موجودة علي اليمين تنزل تحت‬
‫‪ )6‬دائما و ابدا الكربونة االخيرة ‪ CH2OH‬هنحطها فوق الشكل الحلقي‬
‫‪Glucose‬‬
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Galactose
Fructose
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Monosaccharide derivatives
1) Deoxy sugar
➢ These are sugars in which OH group of C2 is replaced by hydrogen.
➢ Example: Ribose is converted into deoxyribose
Ribose
Deoxy-Ribose
2) Amino Sugars
• They are produced by replacing OH group on C2 by
an amino group (NH2).
• Example : glucosamine & mannosamine
3) Amino sugar acids
Pyruvic
acid
➢ These are formed by addition of acids to amino sugars.
➢ 6 carbon amino sugar + 3 carbon acid = 9 carbon amino sugar acid
a) Neuraminic acid: mannosamine and pyruvic acid
b) sialic acid: N Acetyl Neuraminic Acid (NANA):
present in glycolipids (gangliosides)
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4) sugar alcohols
➢ Reduction of monosaccharides gives sugar alcohols.
a) Ribose gives ribitol,
b) Glucose gives sorbitol (used to relieve constipation),
c) mannose gives mannitol, (used as a diuretic, to help the body produce more urine
in cases of hypertension and oedema)
d) fructose gives rise to either sorbitol or mannitol.
e) galactose gives galactit ol,
 myoinositol is a cyclic sugar alcohol occurs in nature and is important in formation of
phosphatidylinositol and present in muscle.
5) Sugar acids
• These are oxidation products of monosaccharides.
• Biologically important sugar acids
a) Uronic acids:
o obtained by oxidation of the last carbon
o e.g. D-glucose yields D-glucuronic acid (it is important as a component of
mucopolysaccharide and also in detoxication processes).
b) L-ascorbic acid (vitamin C) is another important naturally occurring sugar acid.
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Disaccharides
• Formed by condensation between 2 monosaccharides.
• The bond between them is called glycosidic bond.
1) Maltose
 Maltose is called malt or corn sugar
 Structure: 2 α-glucose linked by α-1,4 glycosidic bond
α-glucose
α-glucose
Maltose (has free anomeric carbon & Reducing)
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2) lactose
 Lactose is called milk sugar (it make up around 4.5 – 5 % of milk)
 Lactose is non fermentable.
 Structure: β-galactose + β-glucose linked by β-1,4 glycosidic bond
β-galactose
β-glucose
Lactose
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3) Sucrose
 Sucrose is called table sugar or sugar beets oe sugar cane
 Structure: α-glucose + β-fructose linked by α-1 and β-2 glycosidic bond
4) lactulose
• Structure: β-galactose and β- fructose linked by β 1,4 glycosidic bond.
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Disaccharides
Maltose
Lactose
Sucrose
1. Table sugar
2. Cane
3. Honey
4. beet
α-glucose + β-fructose
Sources
1. Malt
2. Germinating cereals
3. Action of amylase on starch
Milk
Structure
Bond
α-glucose + α-glucose
β-galactose + β-glucose
α-1,4 glycosidic bond
β-1,4 glycosidic bond
• α-1 and β-2 glycosidic bond
• α-1, 2 glucosidic bond
• β- 2, 1 fructosidic bond
Has free anomeric
1) show α & β
2) reducing sugar
3) formation of osazone
NO free anomeric
1) NO α & β
2) Not reducing sugar
3) No osazone
Free anomeric Has free anomeric
1) show α & β
2) reducing sugar
3) formation of osazone
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Homopolysaccharides
• Composed of repeated units of similar monosacchrides.
Site
Function
1- Glycogen
2- Starch
3- Cellulose
Liver & muscle
The storage form of
carbohydrates in
animals
Cereals, potatoes & vegetables
Wall of Plant cell
Prevent
constipation
The storage form of carbohydrates in
plants
Amylopectins
Structure
Highly branched
Outer part (80%)
molecule consists of αglucose units linked by Each chain composed of
20-30 glucose units
α-1,4 glycosidic bonds
linked by α 1,4
at straight chains
glycosidic bonds at
and α 1,6 glycosidic
straight chains and
bonds at branched
α 1,6 glycosidic bonds
points.
at branched points.
Amylose
Inner part (20%)
Contains only
α 1,4
glycosidic
bonds
with no
branches
β- gluose units
linked by β 1,4
glycosidic bonds
with no branches
Functions of cellulose:
➢ Cellulose not digested by human bodies due to absence of hydrolytic enzymes that
attack β-link. So it prevents constipation as it forms the main bulk of stool (but digested
by cows (ruminanats)
N.B.
1) Maltose results from Partial hydrolysis of starch by amylase enzyme in saliva.
2) Glucose results from complete hydrolysis of starch
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Sulfate free
Hyaluronic
acid
Sulfated
Chondroitin
Sulfate:
Keratan
sulphate:
Heparan
sulphate
Dermatan
sulphate
CHEMISTRY
• Repeated disaccharide units of :
a) Glucuronic acid
b) N-acetyl D glucosamine
linked by O-glycosidic bonds.
CHEMISTRY
IMPORTANCE
• lubricant and shock
absorber In synovial fluid
and loose connective tissue
IMPORTANCE
• Repeated disaccharide units of :
a) D-glucuronic acid
b) N-acetyl-D-galactosamine
sulphated.
• Repeated disaccharide units of :
a) D-galactose
b) N-acetyl D-glucosamine
Main GAG in bone and
cartilage
• Sulphate may be present on either
sugar.
• No uroni acid.
• Also present in loose
connective tissue and
cartilage
• present in cornea and
important for
transparency of cornea
• Repeated disaccharide units of :
• cell membrane receptors,
a) D-glucuronic acid sulphate or • cell-cell interaction,
L-iduronic acid sulphate.
• controlling cell
b) D-glucosamine disulphate
differentiation
• tissue morphogenesis and
homeostasis
• Repeated disaccharide units of :
• present in blood vessels,
a) L-iduronic acid mainly with
heart valves and skin
variable amount of D• maintenance of shape of
gulcuronic acid
the sclera of the eye
b) N-acetyl D-galactosamine
sulphate
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 GAGS have negative charges , so repel each other
 They produce slippery consistency of mucous sercretion and synovial fliud
 When GAGS is compressed, water is squeezed out and GAGs occup small volume and vice
versa
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function of carbohydrates
1) storage form of energy in the body
2) provide a significant fraction of calories for most organisms
3) in cell membrane → mediate intracellular communications
4) structural components of many organism
• cell wall of bacteria
• exoskeleton of inscts
• cellulose of plant
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