carbohydrate
DESCRIPTION
BiokimiaTRANSCRIPT
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Carbohydrates Carbohydrates :: Physical and Chemical PropertiesPhysical and Chemical Properties
ByBy
drg. Prasetyo Adi, MSdrg. Prasetyo Adi, MS
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ObjectivesTo Understand :• The importance of carbohydrates for
organisms• The classification of carbohydrates• The physical and chemical
properties of carbohydratesReference :• March and Bettelheim,1995;
Introduction to General,Organic & Biochemistry, 4th edition, Saunders College
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What’s carbohydrate ?
• Compound containing C, H, O
• General formula : Cx (H2O)y
• Polyhydroxylated aldehydes aldose
• Polyhydroxylated ketones ketose
• In plants, simple carbohydrate (glucose) is synthesized from carbon dioxide and water by photosynthesis
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CARBOHYDRATES:
• POLYHYDROXY ALDEHYDES OR KETONES
• SIMPLE CARBOHYDRATES MOLECULES ARE SYNTHESIZED
CHIEFLY BY CHLOROPHYL-CONTAINING PLANTS AS LONG
AS THE SUN IS SHINING
6 CO2 + 6 H2O C6H12O6 + 6 O2 LIGHT
KHOLOROFIL
PHOTOSYNTHESIS
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The Importances of carbohydrates
• Give structure to cell walls and cell membrane (e.g. cellulose)
Humans:• Provide the majority of energy • A source of carbon atoms for
synthesis of many compounds nucleic acids and connective
tissue• Comprise large portions of nucleic
acids that form DNA and RNA (e.g. ribose, deoxyribose)
• Comprise some portions of connective tissues
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Classification
Based on :
1. Number of sugar units in total chain
2. Number of carbon atoms in the chain
3. Stereochemistry
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Classification of carbohydrate based on the number of sugar units :
• Monosaccharides : single sugar unit
e.g. glucose, fructose, galactose• Disaccharides : 2 sugar units
e.g. lactose, sucrose• Oligosaccharides : 3-10 sugar units
e.g. maltotriose• Polysaccharides : > 10 sugar units
e.g. starch, cellulose
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Monosaccharides classifisation based on the number of carbon atoms
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Stereoisomer
• Stereochemistry : study of the spatial arrangement of the molecules
• Stereoisomers have :
- the same order and types of bonds
- different spatial arrangements
- different properties
• Many biologically important chemicals, like sugars, exist as stereoisomers.
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Enantiomers
• Pairs of isomers (stereoisomers)
• that are nonsuperimpossable mirror images of each other
• It must have at least 1 assymmetric carbon
( a chiral carbon)
H
C
FOH
Br
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CH3CH2 CH3CH2
BrBr
H H
Mirror
CH3CH2
Br
H
CH3CH2
H
Br
HH
H
H
a non chiral C
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CH3
CH3CH2 CH3CH2
CH3 Br
Br
H H
Mirror
CH3CH2
CH3
Br
H
CH3CH2
CH3
H
Br
Chiral C
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Functional groups
Double bond
Hydroxyl
Carbonyl
Carboxyl
Sulfhidril
Amine
C C
OH
C O
C
O
OH
SH
NH2
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C
CH OH
CH OH
OH
H
D(+) GLISERALDEHID
H2C
C
CH OH
OH
H
DI HIDROKSIASETON
O
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Aldehyde ( aldose ) derivates :
C
CH OH
CH OH
O
H
HD(+) GLISERALDEHID
C
CH OH
C
CH2OH
H OH
C
CHO H
C
CH2OH
H OH
O O
H H
D(-) ERITHROSE D(-) THREOSE
C
C
C
C
C
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C
CH OH
C
C
H OH
O
H
CH2OH
OHH
C
CHO
C
C
H OH
O
H
CH2OH
OHH
C
C
C
C
O
H
CH2OH
OHH
C
CH OH
C
C
HO H
O
H
CH2OH
OHH
H H
HHO
HO
D-RIBOSE D-ARABINOSE D-XILOSE D-LIXOSE
C
C C
C CC
C
C
C
C
C
C
D - Alosa
D - Altrosa
D - Glukosa
D - Manosa
D - Gulosa
D - Idosa
D - Galaktosa
D - Talosa
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Structure of carbohydrates
• Open Chain Forms • Cyclic Forms
OH
OH
H
OHH
OH
CH2OH
HH
OH
Glucose
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PHYSICAL PROPERTIES OF MONOSACCHARIDES
• sweetness
• solubility
• optical rotation
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Table. Comperative Sweetness of Some Sugars and Artificial Sweeteners.
Sugar or Artificial Sweetness Type
Sweetener Relaitive to Sweeteners
Lactose 0,16 Disaccharide
Galactose 0,32 Monoccharide
Maltose 0,33 Disaccharide
Glucose 0,74 Monoccharide
Sucrose 1,00 Disaccharide
Invert sugar 1,25 Mixture of Glucose and Fructose
Fructose 1,74 Monoccharide
Aspartame 100 –150 Artificial sweetener
Acesulfame-K 200 Artificial sweetener
Saccharin 450 Artificial sweetener
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Solubility
• At room temperature : carbohydrates are solids• Because of the many –OH groups as well as the oxygen
of the aldehyde or ketone groups carbohydrates are soluble in water
these groups form hydrogen bonds with the solvating water molecules
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Optical Rotation
• All three forms of D-glucose (alpha, beta, and open-chain) rotate the plane of polarized ligth to the right D-(+)-glucose
• L-glucose rotate the plane of polarized ligth to the left L-(-)-glucose
• There is no simple relationship between configuration and rotation
• D-(+)-glucose = dextrose• D-(-)-glucose = levulose
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CHEMICAL PROPERTIES OF MONOSACCHARIDES
• Cyclic forms
• Oxydation
• Glycoside formations
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C
CH
C
C
HO
OH
D(+) Glucose
C
OH
H
OH
OH
CH2OH
H
H
CH2OH
C
C
C
HO
C
O
H
OH
OH
CH2OH
H
H
D-Fructose
O H
OH
H
OH
H
OH H
OH
CH2OH
H
OH
CH2OH
H
CH2OH
OH H
H OH
O
Pyranose Furanose
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C
H
OH
H
OHH
OH
H
HO
CH2OH
O
H Rotate C4 - C5
OH
OH
H
OHH
OH
CH2OH
H
C
OHH
OH
H
OHH
OH
CH2OH
HO
H
H
OH
O
OH α
β
O
OH
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Oxidation
• All of monosaccharides are reducing sugars
• Aldehydes and –OH groups are easily oxidized
• Aldehydes are oxidized to carboxylic acids
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Dissaccharides • 2 units of monosaccharides
• Glycoside bonds • From carbon 1 to - OH groups (C4 position).
• α or β position from C1 of 1st unit 1 to –OH group C4 of 2nd unit
1,4’- α or 1,4’- β linkage
O
H
HO
H
HO
H
H
OHHO
OH
O
H
H
HO
H
OHH
OH
OH
12
4
3
5
6
4
3
5
6
21
1,4’- β linkage
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Maltose.• It is a dissaccharide
• Contains 2 glucose units connected in a 1 4 linkage, from hydrolisis of starch by enzymes/acid
• Ex. : • Enzyme α 1,4 - glukan 4- glucanohydrolase in saliva • Enzyme α 1,4 - glukan maltohydrolase in malt
1 Maltose α - glukosidase 2 D-Glucose
O
H
HO
H
HO
H
OHH O
H
O
H
HO
H
OHH OH
H
HOH2C
HOH2C1
2
3
54
6
4
32
1
5
6
1,4’- linkage
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Cellubiose • A dissaccharide
• From hydroliysis of cellulose by enzyme β-glukosidase
• Connected by 1,4 β glycoside linkage
• Cellubiose hydroliysis with acid produces α and β-D-glucose
OHO
H
HO
H
OHH
O
H
HO
H
OHH OH
O
HOH2C HOH2CH
H
H
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Lactose• A dissaccharide
• Connected by 1,4 β glycoside linkage
• Lactose hydrolysis D - glucose and D - galactose,
D - glucose • Source : * mammalian milk 5% Lactose
O
OH
H
H
HO
H
H
OHH
HOH2CO
H
O
H
HO
H
OH
OHH
HOH2C
H
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Sucrose.• Contains : glucose and fructose.
• The glycoside linkage is from C-1 of D-glucose (an aldose) to C-2 of D-fructose (a
• The differences of sucrose from other dissaccharides are :
1. There are 2 anomeric carbon that used for glycoside linkage.
2. Glucose and fructose in sucrose have no hemiacetal group, because sucrose isn’t an equilibrium state with forms aldehyde or keton in water .
3. Sucrose have no mutarotation and isn’t reducing sugar.
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OH
OH
H
H
OHH
OH
H2OH
CH2OHH
CH2OH
OH H
H OH
O
O
ALPHA-GLUKOPIRANOSE
BETA-FRUKTOFURANOSE
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Poly saccharide • Repeated condensation of 1,4 -D-glucose
• Polyglucose
• Contains 1000 to 2000 glucose units
• It has α 1,4 glycoside linkage
1. Amylose
• It has flexibility to form conformation
Coil / helix
O
O
O
o
o
O O
O
HO
O O
O
Amylose
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2. Amylopectin. • A polymer of α -D- glucose
• It isn’t entirely a straight-chain molecule, but has random branches with α 1,6 glycoside linkage
• There are 20 – 25 glucose units in the straigth chain form with α 1,4 glycoside linkages
• Test with Iodine ( I2 ) gives deep
purple colour.
• A Macromolecule contains 105
to 106 glucose units
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O
OH
OH
CH2OHO
OH
OH
CH2OH
O
OH
OH
CH2
O
OH
OH
CH2OH
O
OO
O O
On
n
Amylopectin
Glycogen ( also called animal starch)
Glycogen is similar to amylopectin, has α 1,6 glycosidic linkage at branching points and α 1,4 glycosidic libjkage at the straigth-chain portions.
The structural difference between glycogen and amylopectin is in the degree of branching. There are 10 to 12 glucose units at straight chain.
It is a “giant molecule”, containing about 106 glucose units.
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Cellulose.
• A linear polymer containing D-glucose units, all in the 1,4 glycosidic linkage
• The structural difference between cellulose and amylose : in cellulose all the 1,4 glycosidic linkages are β.
• Cellulose is the most abundant molecule in living tissues.
O
OH
OH
CH2OHO OH
OH
OH
CH2OH
O
OH
OH
CH2OHO
O
OH n Cellulose
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Acidic Polysaccharides
•The tissues are matrix between organs and cells that provides:
• The important role : in the structure and function of connective tissue
• mechanical strength
• filters the flow of molecular information between cells.
Specialized form
Examples :
Cartilage, bone, synovial fluid, skin, tendons, blood vessel walls, intervertebral disks and cornea.
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Hyaluronic acid.
• A typical and the simplest (structurally) acidic polysaccharide of connective tissue
• A “ giant molecul “ : molecular weigth 105 – 107, contains from 300 to 100 000 repeating units, depending the organ in which it occur.
• Most abundant in embryonic tissue and in specialized connective tissues such as :
- The synovial fluid : acts as lubricant
- The vitreous of the eye : its function is to provide a clear, elastic gel that maintains the retina in its proper position.
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Molecular structure of hyaluronic acid :
Composed of D – glucuronic acid linked to N – acetyl glucosamine by β 1,3 linkage, the latter in turn is linked to
the next glucuronic acid by β 1,4 linkage.
O
NH
CH2OHO
OH
OH
CH2OH
O
OH
OH
CH2OH
O
O
O
CCH3
O
OH
O nGlucoronic acid
Glucoronic acid
N-Acetylglucosamine
Hyaluronic acid
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Heparin. • It is one of the most acidic polysaccharides, ocuurs in such tissues as lung, liver, skin and intestinal mucosa
• Biological function : anticoagulant activity prevents blood clotting.
O
OSO3-
OH
C
OO
O
NHSO3H
OH
CH2OSO3H
O
OO-
HEPARIN
O
OSO3-
OHCOO-
NH
OSO3-
CH2OSO3-
O
C O
CH3
O
n
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