Académique Documents
Professionnel Documents
Culture Documents
Carbohydrates
and
their Structures
Maria Salvacion A. Esmalla, M. Sc.
University of Santo Tomas
Faculty of Pharmacy
Biochemistry Department
BIOCHEM LABORATORY
BIOCHEM LABORATORY
OH
Polysaccharide
CH2OH
O
OH
CH2OH
O
OH
OH
CH2OH
O
OH
CH2OH
O
OH
OH
OH
CH2OH
O
OH
CH2OH
O
OH
OH
OH
OH
BIOCHEM LABORATORY
Ketose
CH2OH
CH
H
OH
CH2OH
CH2OH
BIOCHEM LABORATORY
pentose
hexose
BIOCHEM LABORATORY
CHO
H
C
H
C
OH
OH
H
CH2OH
Triose
CHO
H
C
OH
CH2OH
Tetrose
CHO
OH
OH
OH
H
H
H
CHO
C
OH
OH
OH
OH
CH2OH
Pentose
CH2OH
Hexose
BIOCHEM LABORATORY
Fischer Projection
two-dimensional representation of the stereochemistry of
three-dimensional molecules
H
H
HO
H
H
CH2OH
OH
H
OH
OH
CH2OH
D-Glucose
HO
H
H
3
4
5
OH
OH
CH2OH
D-Fructose
BIOCHEM LABORATORY
D, L Notation
D,L tells which of the two chiral isomers we
are referring to.
If the OH group on the next to the bottom
carbon atom points to the right , the isomer
is a D-isomer; if it points left, the isomer is L.
The D form is usually the isomer found in
nature.
BIOCHEM LABORATORY
D Notation
H C
H C OH
H C OH
CH2OH
Right = D
BIOCHEM LABORATORY
BIOCHEM LABORATORY
BIOCHEM LABORATORY
CHO
H
CHO
OH
CH2OH
D-Glyceraldehyde
HO
CH2OH
L-Glyceraldehyde
BIOCHEM LABORATORY
CHO
H
CHO
OH
CH2OH
D-Glyceraldehyde
HO
CH2OH
L-Glyceraldehyde
BIOCHEM LABORATORY
H
C
C
H
OH
HO
OH
OH
CH2OH
D-Erythrose
CH2OH
D-Threose
BIOCHEM LABORATORY
H
C
C
H
OH
OH
OH
HO
OH
OH
CH2OH
D-Ribose
CH2OH
D-Xylose
BIOCHEM LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Important Monosaccharides
H
CH 2OH
C
OH
HO
HO
OH
OH
OH
OH
CH 2OH
D-Glucose
CH 2OH
D-Fructose
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Important Monosaccharides
H
O
C
H C OH
HO C H
HO C H
H C OH
CH 2OH
D-galactose
BIOCHEM LABORATORY
H
HO
H
H
OH
6
6
CH2OH
OH
OH
C
OH
CH2OH
D-Glucose
C
OH
H
H
O
H
C2
OH
H
1
C
O
CH2OH
C
OH
H
C
OH
O
H
C2
OH
Hemiacetal form
H
C
OH
BIOCHEM LABORATORY
CH2OH
HO
H
H
O
H
OH
OH
CH2OH
D-Fructose
C
4
CH2OH
CH2OH O
C
OH C
OH
CH2OH
CH2OH O
C
H
H
C
OH
OH C
C
OH
Hemiketal form
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
(36%)
D-glucose (open)
(trace)
-D-glucose
(64%)
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Mutarotation
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Mutarotation
BIOCHEM LABORATORY
H
4
C
OH
CH2OH
C
OH
H
C
H
O
H
C2
OH
H
C
Anomeric
carbon
5
OH
CH2OH
CH2OH O
C
H
H
C
OH
OH C
C
OH
Anomeric
carbon
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
H
4
C
OH
C
OH
H
CH2OH
O
H
C2
OH
-D-Glucose
H
C
H
1
OH
C
OH
CH2OH
C
OH
H
O
H
C2
OH
-D-Glucose
OH
C
H
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Haworth Projection
perspective representation of the cyclic forms of sugars
O
C
C
C
C
Furanose structures
Furan
C
C
Pyranose structures
Pyran
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
OH
OH
H
CH2OH
OH
OH
H
OH
3
H
1
OH
5
4
OH
-D-Glucose
CH2OH
D-Glucose
O
1
OH
3
OH
OH
CH2OH
(-D-Glucopyranose)
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Conformation
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
CH2OH
5
H
OH
OH
O
H
H
1
OH
OH
-D-Glucose
(-D-Glucopyranose)
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
CH2OH
CH2OH
O
+
OH
OH
OH
OH
Glycosidic bond
CH3OH
OH
OH
OCH3
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
CH2OH
O
CH2OH
OH
OH
OH
O
OH
OH
OH
OH
OH
H2
C
OH
OH
OH
CH2OH
O
OH
OH
O
O
CH2OH
OH
OH
OH
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Important Disaccharides
Maltose = Glucose + Glucose
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Important Disaccharides
CH2OH
CH2OH
CH2OH
OH
OH
O
OH
OH
D-Lactose
CH2OH
CH2OH
O
OH
OH
O
OH
OH
CH2OH
O
OH
OH
OH
OH
OH
Sucrose
CH2OH
CH2OH
OH
OH
OH
CH2OH
OH
OH
O
O
OH
OH
OH
-D-Maltose
D-Cellobiose
OH
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Sucrose
CH 2OH
o
OH
OH
, -1,2-glycosidic
bond
OH
CH 2OH
O
OH
OH
CH 2OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Lactose
(1-4) glycosidic bond
CH2OH
CH2OH
O
OH
O
O
OH
OH
OH
OH
OH
D-Lactose
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Maltose
(1-4) glycosidic bond
CH2OH
CH2OH
O
OH
OH
O
OH
OH
OH
OH
-D-Maltose
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Cellobiose
(1-4) glycosidic bond
CH2OH
CH2OH
O
OH
OH
OH
OH
OH
D-Cellobiose
OH
Learning Check
Identify the monosaccharides in each of the
following:
A. lactose
(1) glucose
(2) fructose (3) galactose
B. maltose
(1) glucose
C. sucrose
(1) glucose
Solution
A. lactose
(1) glucose and (3) galactose
B. maltose
(1) glucose and (1) glucose
C. sucrose
(1) glucose and (2) fructose
40
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Important Polysaccharides
Starch
Amylose
Amylopectin
Glycogen
Cellulose
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Polysaccharides
Polymers of D-glucose
6
CH2OH
H
4
C
OH
C
OH
H
O
H
C2
OH
H
C
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Amylose
Polymer with -1,4 bonds
CH2OH
CH2OH
O
CH2OH
O
OH
OH
OH
O
OH
CH2OH
OH
O
OH
O
OH
-1,4 bonds
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Amylopectin
Polymer with -1,4 and -1,6 bonds branches
-1,6 bond
CH2OH
CH2OH
O
CH2OH
O
OH
OH
OH
OH
OH
CH2OH
OH
CH2OH
CH2
O
OH
OH
OH
O
OH
CH2OH
OH
O
OH
-1,4 bonds
O
OH
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Cellulose
Polymer with -1,4 bonds
CH2OH
O
OH
CH 2OH
O
OH
OH
CH2OH
O
O
OH
OH
O
OH
-1,4 bonds
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Glycogen
Learning Check
Identify the polysaccharide in each as:
1) starch 2) glycogen 3) cellulose
A.
B.
C.
47
Solution
3) cellulose
1) starch
2) glycogen
48
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Physical Properties
of
Carbohydrates
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Physical Properties
Carbohydrates are solid at room temp
Mono- and disaccharides are white crystalline substances
and soluble in H2O
Starches are amorphous and slighlty soluble in H2O
Cellulose is fibrous and insoluble in H2O
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Chemical Properties
of
Carbohydrates
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Reducing Property
1.
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Reducing Property
2.
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Reducing Property
3.
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Isolation
of
Carbohydrates
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Hydrolysis
of
Carbohydrates
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Acid Hydrolysis
- 2 N HCl
- complete hydrolysis
- efficient method to obtain monosaccharides
starch/glycogen
glucose
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Enzymatic Hydrolysis
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Enzymatic Hydrolysis
- salivary amylase (-amylase)
- very specific
- an endoglycosidase hydrolyzing -1,4 linkages at random
to yield a mixture of glucose, maltose, dextrin & other
hydrolysates
starch/glycogen
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Rf
polar
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Quantitative Determination
of
Carbohydrates
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Nelsons Test
REAGENTS: Nelsons A Na2CO3, NaKtartrate, NaHCO3, Na2SO4
Nelsons B CuSO45H2O, H2SO4
Arsenomolybdate reagent
- CuSO4 serves as the oxidizing agent
- Na2CO3 & NaHCO3 makes sugars more reactive
- NaKtartrate prevents the precipitation of Cu(OH)2
- NaKtartrate would tend to reduce Cu2+ in time
- Arsenomolybdate is added to dissolve Cu2O & is converted into molybdenum blue
- color intensity of molybdenum blue A480
y = mx + b
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
Characterization
of
Carbohydrates
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
I2
I2
I2
I2
HEAT
I2
COOL
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
OH
H
CH O
[O]
H
H
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
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LABORATORY
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LABORATORY
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BIOCHEM
LABORATORY
H
C
H
HO
HO
H
C
C
H2C
1
2
OH
OH
OH
HO
HNO3
OH
2
HO
O
OH
OH
HO
O
6
5
OH
OH
BIOCHEM LABORATORY
BIOCHEM
LABORATORY
BIOCHEM LABORATORY
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LABORATORY
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LABORATORY
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LABORATORY
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