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Monosacharides 2015
Monosacharides 2015
Monosacharides 2015
Biology
CARBOHYDRATE CHEMISTRY
By
2
Ayman Elsamanoudy
Objectives (ILOs)
I. to study the definition, classification of
carbohydrates
II. to know the biological importances of
carbohydrates.
III. to know the important body structure formed
by carbohydrate molecules and study its
functions .
IV. to understand how any disorder in
carbohydrates structure or function leads to
disease.
3
Carbohydrates are :
Organic compounds composed of C.H.O.
Contain more than hydroxyl group.
Contain active carbonyl group ;aldehyde at C1 or
ketone group at C2.
Generally but not always the hydrogen and oxygen
in carbohydrates are present in the proportion of
2H and one oxygen atoms as in water.
4
Definition:
Carbohydrates are polyhydroxy aldehydes or
polyhydroxy ketones and compound giving them
on hydrolysis
5
Function of carbohydrates
1. They serve as energy stores and fuels.
2. They enter in the structure of cell membranes.
3. Pentose sugars (ribose and deoxyribose) enter in the
structure of nucleic acids.
4. Carbohydrates enter in the structure of glycoproteins and
glycolipids.
5. Carbohydrates play important roles in recognition
between cell types or recognition of cellular structures by
other molecules.
NB: Recognition events are important in normal cell
growth, fertilization and transformation of cells.
6
Classification
Monosaccharides Disaccharides Oligosaccharides Polyosaccharides
Diff The simplest 2 monsacch. 3-10 monsacch. Units linked to More than 10
carbohydrates. Units linked to each other by glycosidic bond monsacch. Units
each other by linked to each other
They contain only
glycosidic bond by glycosidic bond
one sugar unit .
-cannot be
hydrolysed into
simpler units
Ex. Glucose …. Sucrose & 1-Maltotriose = 3 glucose units Starch …….
Lactose……
2-Raffinose
(tri-saccharide=
glucose+glactose+fructose)
7
Monosaccharides
4 Ketotetrose
Aldotetrose
(Tetrose) Tetrulose
5 Ketopentose
Aldopentose
(Pentose) Pentulose
6 Ketohexose
Aldohexose
(Hexose) Hexulose
10
Aldoses
Ketoses
12
Structural formula of monosaccharides
A) Straight (open) chain formula :
B) Cyclic structural formula .
1-Fischer projection form:
2-Haworth form
1-simple chain 2- Cyclic structure formula:
formula
In the solution, the sugar which has an aldehyde group undergoes the
structure .
a-Fischer projection formula:the b- Haworth formula:
(or)
CH
Furan ring
HO C
HO C
H C
H C
CH
CH2OH CH2OH
C=O HO C OH
(or) -D-F
HO C H + H2O HO C H OR +
H C OH H C OH CH
H C OH H C OH HO C
CH2OH CH2OH HO C
D-Fructose D-Fructose ketonol, H C
unstable H C
O H2C
(or) -D-
Pyran ring
Then
2- The OH group from the aldenol group condenses
with the OH :
on C4 or C5 of the aldo-sugar to forms a ring or
hemi-acetal structure with the liberation of H2O
again.
Keto-sugar condenses only with C5 or with C6
giving Hemiketal form .
17
The aldehyde or
ketone group can react
with a hydroxyl group
to form a covalent
bond.
An aldehyde reacts
with a hydroxyl group
creates a hemiacetal.
A ketone reacts with a
hydroxyl group to
form a hemiketal.
19
Haworth's formula:
Because Fisher’s formula could not explain some of
the chemical and physical characteristics of sugars,
Haworth put forth his formula.
. C and O atoms of the ring are drawn in the plane of
the page.
H and OH or other side groups are written on
perpendicular plane.
All groups located on the left side of fisher’s are
written upwards. All groups located on the right
side of fisher’s are written downwards Except in
Last C in the ring .
5 membered oxy ring 6 membered oxy ring
22
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MCQs
25
A triose sugar is
(A) Glycerose
(B) Ribose
(C) Erythrose
(D) Fructose
A pentose sugar is
(A) Dihydroxyacetone
(B) Ribulose
(C) Erythrose
(D) Glucose
26
. Ribulose is a these
(A) Ketotetrose
(B) Aldotetrose
(C) Ketopentose
(D) Aldopentose
27
Which of the following is a keto sugar
A) Galactose
B) Fructose
C) Glucose
D) Mannose
28
Glycosidic bond is absent in
A) Disacharide
B) oligosacharide
C) Monosacharide
D) Polysacharide
29
Hydration of glucose leads to formation of
A) Stable alcohol
B) Unstable aldenol form of glucose
C) Direct cyclization of glucose
D) No effect
30
Fructofuranose is
A) Straight chain formula of
fructose
B) Fischer projection formula of
fructose
C) Ketenol form of fructose
D) 6 membered oxy ring of
fructose
31
The predominant form of glucose in
solution is
(A) Acyclic form
(B) Hydrated acyclic form
(C) Glucofuranose
(D) Glucopyranose
32
Asymmetric carbon atom (chiral carbon)
33
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Optical activity
35
Types of optically active sugar solutions
A. If the compound rotate plane polarized light to the right, it
is called >>>>dextrorotatory, d or (+).
Example: Glucose is dextrorotatory so it is sometimes called
dextrose.
B. If the compound rotate plane polarized light to the left, it
is called>>>>>. levorotatory, l or (-).
Example: Fructose is levorotatory so it is sometimes called
levulose.
NB :All monosaccharides are optically active, except
dihydroxy acetone, this is due to the presence of
asymmetric carbon atoms.
36
Measurement of optical activity
By : Polrimeter or Polriscope
Composition :
1- source of light (Na light).
2-A Nicol prism(polarizer):it converts ordinary
scattered light into PPL.
3- A glass tube in which the exmined solution will
be done.
4- Analyzer which determine the angel of rotation.
5- Detector
37
38
39
Specific rotation
It is the angle of rotation specific for each
optically active substance when the
concentration of substance is 100 g/dl and the
length of measuring tube is 10 cm using Na
light at 20 Ċ.
Examples :
The specific rotation :
1. for glucose is + 52.5 &
2. for fructose is - 91.
40
Factors affecting specific rotation
1. Type of light.
2. Length of the tube.
3. Nature and concentration of substance.
4. Temperature.
41
Optical isomerism
Def :Compounds having the same structural
formulae (same chemical group) but differ in the
way these groups are attached in space around only
one of its asymmetric carbon atom.
42
Types of isomerism of monosacharides:
43
Enantiomers: (D & L) isomers
Concept: Two isomers which are mirror images .
Reffered to : prelast carbon which is the last asymetric
C atom .
Types of enantiomers :
1- D form: OH attached to the right of prelast C.
2-L form: OH attached to the left of prelast C
Description :They differ in all carbons (mirror image)
but D & L configuration is according to H – OH
orientation in the pre-last C.
NB: The great majority of the sugars in humans are D-
sugars
44
45
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47
48
Anomers :α and β isomer
Concept:These are isomers that differ in position of OH
group at the anomeric carbon atom.
Reffered to: anomeric C atom
Def of annomeric C atom: is the asymmetric carbon atom
obtained from active sugar group in the cyclic structure .
Position of anomeric C:C1 in aldose and C2 of ketose).
Types of anomers :
1- α sugar : OH group attached to the anomeric carbon is
on the right side.
2- β sugar. OH group attached to the anomeric carbon is
on the left side.
49
50
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Epimers
Concept :If two monosaccharides differ in
configuration around only one asymtetric carbon
atom other than anomeric C& the prelist C atom
,((the epimeric carbon))>>>> they are defined as
epimers of each other.
Referred to: epimeric carbon .
Def of epimeric carbon : asymtetric carbon atom
other than anoneric& the prelist C atoms.
Examples : usually erpimers are described in pairs :
. Glucose & galactose are C4 epimer. .
53
Glucose & mannose are C2 epimer
54
55
Aldose and ketose isomers
56
57
Pyranose and furanose isomers
58
59
60
MCQs
The number of isomers of glucose is
(A) 2
(B) 4
(C) 8
(D) 16
61
Isomers differing as a result of
variations in configuration of the —OH
and —H on carbon atoms 2, 3 or 4 of
glucose are known as
(A) Epimers
(B) Anomers
(C) Optical isomers
(D) Steroisomers
62
The most important epimer of glucose is
(A) Galactose
(B) Fructose
(C) Arabinose
(D) Xylose
63
-D-glucose and -D-glucose are
(A) Stereoisomers
(B) Epimers
(C) Anomers
(D) Keto-aldo pairs
64
Which of the following is an epimeric pair?
(A) Glucose and fructose
(B) Glucose and galactose
(C) Galactose and mannose
(D) Lactose and maltose
65
Sugar Derivatives
They include:
I. Sugar Acids.
II. Sugar Alcohols.
III. Deoxysugars.
IV. Amino Sugars.
V. Amino sugar acids.
66
Sugar Acid.
Def: They are the oxidation products of monosaccharides
67
1.Aldonic
CHO COOH
H C OH H C OH
HO C H bromine water, O2 HO C H
H C OH H C OH
H C OH H C OH
CH2OH CH2OH
D-Glucose D-Gluconic acid
2-Uronic
CHO CHO
H C OH H C OH
HO C H H2O2 HO C H
CH2OH COOH
D-Glucose D-Glucuronic acid
3-Aldaric
CHO COOH
H C OH H C OH
HO C H O2 HO C H
H C OH Conc. Nitric acid H C OH
H C OH H C OH
CH2OH COOH
D-Glucose D-Glucaric acid
COOH CHO
H C OH H C OH
HO C H HO C H
H C OH H C OH
H C OH H C OH
CH2OH COOH
71
Imortance of Iduronic acid :
glycosaminoglycans formation
(mucopolysaccharides)
74
Ascorbic acid dehydrAscorbic acid
(reduced form) (oxidized form)
75
2-Sugar alcohols (Alditols)
Diff: It is the product of reduction of the active
carbonyl group .
Concept: Aldoses and Ketoses may be reduced at the
carbonyl carbon to the corresponding polyhydroxy
alcohols (sugar alcohols).
Examples :
D-glucose D-sorbitol.
D-mannose D-mannitol.
D-fructose D-sorbitol and D-mannitol.
D-galactose D-galacticol.
D-ribose
76 D-ribitol
CHO CH2OH
H C OH H C OH
H C OH
H2
H C OH
H C OH Na amalgum, H 2SO4 H C OH
CH2OH CH2OH
Ribose Ribitol
77
CHO CH2OH
H C OH H C OH
HO C H H2 HO C H
H C OH H C OH
Na amalgum, H 2SO4
H C OH H C OH
CH2OH CH2OH
Glucose Sorbitol
CH2OH CH2OH CH2OH
C=O H C OH HO C H
HO C H HO C H HO C H
H2
H C OH OR H C OH
H C OH Na amalgum, H 2SO4
H C OH H C OH H C OH
H 3 2 OH
H H
4 1
OH H
OH 5 6 H
H OH
Inositol
79
3- Deoxysugars
Def:They are monosaccharides with only one of its
hydroxyl groups is replaced by hydrogens i.e. there is only
one oxygen missed.
Examples :
2-Deoxy-D-ribose is a constituent of DNA.
80
Fucose :6 deoxy-galactose ( it is a component of
glycoprotein
81
4- Amino sugars
Def:The hydroxyl group is replaced by an amino group at
the C-2 position.
Importance :Amino sugars are found in
glycosaminoglycans and glycoproteins.
Examples :
D-glucosamine:
It is a constituent of heparin and hyaluronic acid.
D-galactosamine:
It is a constituent of chondriotin sulphate.
Mannosamine
It is a constituent of neuraminic acid and sialic acids
82
CH2OH CH2OH 6CHCHOH2O-SO3H 6
CH2OHO 2 CH2O -
O OO O-SO 3H
H OH
H H OHH H HOH HH HH
H H H
4
H OHOH H H OH
OH HH OH
OH
2 OH OH H 2 2 OHOH OH
H 22 OH
OHH
OH
H HN C CH3 H
H NH2 H H HN CNHCH 2 3 H NH-SO3H
O
- D-galactosamine
O N- acetyl-galactosamine sulfated N
-D-glucoamine N-acetyl-glucosamine sulfated glucosamine galactos
83
5-Amino sugar acids
Def:They are condensation products of amino sugars and
some acids
Example: Neuraminic acid
Discription: It results from a C-C bond between the C-1
of mannosamine and the C-3 of pyruvic acid.
Importance of neuraminic acid
It is amino sugar acid present in neural tissue.
The N-acetyl derivative of neuraminic (NANA) is
called sialic acid, which is widely distributed in
bacteria and animal systems
84
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Monosaccharides of Biological Importance
1) Glucose (Dextrose) (Grape Sugar):
It is the most important and famous sugar
It is the major source of energy in humans and animals.
Ingested carbohydrates are absorbed in the form of
glucose.
It is converted into other sugars in the liver and other
tissues
Examples : galactose, fructose, ribose and glycogen.
86
2)Galactose:
It is synthesized in mammary gland to form the
disaccharide lactose (sugar of milk).
It can be converted into glucose in the liver.
3)Mannose:
It is a constituent of many glycoproteins and
aminosugar acids as sialic acid.
4)Fructose (Levulose) (Fruit Sugar):
It is present in semen
It is a constituent of disaccharide sucrose and
polysaccharide inulin.
It can be
87
converted into glucose in the liver.
5)Ribose and deoxyribose:
They form part of the structural backbone of
nucleic acids RNA and DNA.
6)Ribose enters in the structure of high-energy
phosphate compounds as ATP, GTP and CTP and
also in the structure of coenzymes such as NAD,
NADP, FAD and FMN.
7)Ribose phosphate, Ribulose phosphate, Xylulose
and sedoheptulose are intermediates in
carbohydrate metabolism
88
The sugar found in DNA is
(A) Xylose
(B) Ribose
(C) Deoxyribose
(D) Ribulose
89
Sorbitol is produced by reduction of :
(A) Galactose or fructose
(B) Glucose or galactose
(C) Glucose or fructose
(D) Galactose or fructose
92
8.epimers(def, examples)
9.sugar acids (def,types & example for each)
10. sugar alcohol (def & 3 examples )
11.Deoxy-sugar ( def & 2 different examples and the
importance of each one )
12.Amino acid sugar (def,example).
13.Enumerate the products of hydrolysis of sialic
acid.
14. Enumerate monosacharides of biological
importance
93
GREAT
THANKS
Ayman Elsamanoudy