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Objectives
To Understand : The importance of carbohydrates for organisms The classification of carbohydrates The physical and chemical properties of carbohydrates Reference : March and Bettelheim,1995; Introduction to General,Organic & Biochemistry, 4th edition, Saunders College
Whats 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
CARBOHYDRATES:
POLYHYDROXY ALDEHYDES OR KETONES
PHOTOSYNTHESIS
6 CO2 + 6 H2O
LIGHT KHOLOROFIL
C6H12O6 + 6 O2
Classification
Based on : 1. Number of sugar units in total chain 2. Number of carbon atoms in the chain 3. Stereochemistry
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.
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 F
Br OH
CH3CH2
Mirror
CH3CH2
Br
Br H H
CH3CH2
CH3CH2
a non chiral C
H
H H
Br
Br
CH3CH2
Mirror
CH3CH2
CH3 H
Br
Br
CH3 H
CH3CH2
CH3CH2
Chiral C
H
CH3 H
Br
Br
CH3
Functional groups
Double bond
Hydroxyl Carbonyl Carboxyl C C C
OH
O O C
OH Sulfhidril
Amine SH
NH2
O C H H C OH H C OH H D(+) GLISERALDEHID
H2C C
OH O
H C OH H DI HIDROKSIASETON
O C H
C C
C H
OH OH
D(+) GLISERALDEHID
O C H H H
O C H HO H C C C C H OH
OH OH
CH2OH
D(-) ERITHROSE
CH2OH
D(-) THREOSE
O C H H H H C C OH OH OH HO H H
O C H
O C H H HO H C C C C C C OH H OH HO HO H
O C H C C C C C C H H OH
C C
C C C C
H OH OH
C C
C C
CH2OH
D-RIBOSE
CH2OH
D-ARABINOSE
CH2OH
D-XILOSE
CH2OH
D-LIXOSE
D - Alosa
D - Glukosa
D - Gulosa
D - Galaktosa
D - Manosa D - Altrosa
D - Idosa
D - Talosa
Structure of carbohydrates
Open Chain Forms Cyclic Forms
CH2OH H H OH OH H OH O H OH H
Glucose
Sucrose
Invert sugar Fructose Aspartame Acesulfame-K Saccharin
1,00
1,25 1,74 100 150 200 450
Disaccharide
Mixture of Glucose and Fructose Monoccharide Artificial sweetener Artificial sweetener Artificial sweetener
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
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
O C H H HO H H C C C C OH H OH OH HO H H
CH2OH C C C C O H OH OH
CH2OH D-Fructose
CH2OH H H OH OH H OH O H OH
CH2OH
H
H
O OH
CH2OH
OH OH H
Pyranose
Furanose
H H HO OH OH H OH CH2OH H H C O
Rotate C4 - C5
CH2OH H H OH OH H OH OH H H C O
CH2OH H H OH OH H OH O H
H OH O
O OH
OH
Oxidation
All of monosaccharides are reducing sugars Aldehydes and OH groups are easily oxidized Aldehydes are oxidized to carboxylic acids
Dissaccharides
2 units of monosaccharides
Glycoside bonds From carbon 1 to - OH groups (C4 position). or position from C1 of 1st unit 1 to OH group C4 of 2nd unit
H OH
6 4 5
O
4 1
6 5 3
HO HO
3
H
2
O
1
O HO H
H H
OH H
OH
OH
1,4- linkage
Maltose.
It is a dissaccharide
Contains 2 glucose units connected in a 1 4 linkage, from hydrolisis of starch by enzymes/acid Ex. : Enzyme 1,4 - glukan 4- glucanohydrolase in saliva Enzyme 1,4 - glukan maltohydrolase in malt
1 Maltose
H
4 5 6
- glukosidase
2 D-Glucose
HOH2C H
2
O
1
HO HO
3
H
4
H HOH2C
6 5
H H
OH O
H
2
O
1
HO
1,4- a linkage
H
OH
OH
Cellubiose
A dissaccharide
HOH2C
H H O O HO H H H OH HOH2C H O OH
HO HO H H OH
Lactose
A dissaccharide Connected by 1,4 glycoside linkage
Lactose hydrolysis D - glucose and D - galactose, D - glucose
OH HOH 2C H HO H H OH H H O O HO
H HOH 2C H O H H H OH OH
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 isnt an equilibrium state with forms aldehyde or keton in water .
H2OH H OH OH H CH2OH H H OH H OH O O H H
ALPHA-GLUKOPIRANOSE
BETA-FRUKTOFURANOSE
O OH CH2OH
Poly saccharide
1. Amylose
Repeated condensation of 1,4 a-D-glucose
Coil / helix
HO
Amylose
O O
2. Amylopectin.
A polymer of -D- glucose It isnt entirely a straight-chain molecule, but has random branches with 1,6 glycoside linkage There are 20 25 glucose units in the straigth chain form with 1,4 glycoside linkages A Macromolecule contains 105 to 106 glucose units Test with Iodine ( I2 ) gives deep purple colour.
CH 2OH
CH 2OH
O
O OH OH O OH
Amylopectin
OH O CH 2
n
CH 2OH
O
O OH OH O OH
O
O OH
Glycogen
Glycogen is similar to amylopectin, has 1,6 glycosidic linkage at branching points and 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.
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 . Cellulose is the most abundant molecule in living tissues.
CH 2OH
O
CH 2OH
OH
O
CH 2OH
OH OH
O
OH
OH OH
OH
OH
Cellulose
Acidic Polysaccharides
The important role : in the structure and function of connective tissue
The tissues are matrix between organs and cells that provides:
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.
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.
- The vitreous of the eye : its function is to provide a clear, elastic gel that maintains the retina in its proper position.
Composed of D glucuronic acid linked to N acetyl glucosamine by 1,3 linkage, the latter in turn is linked to
the next glucuronic acid by 1,4 linkage.
N-Acetylglucosamine
CH2OH
O O O
OH OH
CH2OH
CH2OH
OH O NH n C O CH 3
O O
OH OH
Glucoronic acid
Glucoronic acid
Hyaluronic acid
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 C OO OH O OSO3O
CH2OSO3-
OSO3NH C O CH3
HEPARIN