chapter 7 carbohydrates and glycobiology. carbohydrates are everywhere ...
TRANSCRIPT
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Chapter 7
Carbohydrates and Glycobiology
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Carbohydrates are everywhere
http://www.homejoin.com.tw/newpic2000/HST-40.jpghttp://www.cofc.edu/~delliss/virtuallabbook/LoadingGel/Minigel2a.jpg
http://www.99main.com/~charlief/theeyebg.gif http://sportsdrz.com/images/knee.jpg
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Sucrose
http://graphics.stanford.edu/courses/cs348b-competition/cs348b-05/donut/fifthdonut.jpg
http://www.solarnavigator.net/solar_cola/cola_images/sucrose_table_sugar_crystals.jpg
glazed donuts
Sucrose (table sugar)
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What are carbohydrates?
• Carbo-hydrates are a group of organic compound that can usually represented as (CH2O)n. Glucose, fructose, and galactose are all carbohydrates.
-D-Galactose
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Classification of carbohydrate
– carbon number– L- or D- isomers– pyranose or furanose– α or β anomers– ketose or aldose
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Carbon number
• In addition to simple hexose such as glucose, galactose, and mannose, there are a number of sugar derivatives in which a hydroxyl group in the parent compound is replaced with another substituent, or carbon atom is oxidized to a carboxyl group.
• Therefore, researchers must give each carbon of a sugar a number.
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Carbon numberH OC
HCC
H
CH
C
H
CH2OH
HOOH
OH
OH
CH2OH
HCC
H
CH
C
HHO
O
OH
OH
CH2OHaldose ketose
1
2
3
4
5
6
1
2
3
4
5
6
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L- and D- isomers
CHO
H|
-C-|OH
CH2OH
CHO
H|
-C-|
HO
CH2OH
-glyceraldehydeD -glyceraldehydeL
[]25D=+8.7˚ []25
D=-8.7˚
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L- and D-isomers
• Although L- and D-isomers of glyceraldehydes are truly levo-rotatory (-) and dextro-rotatory (+), L- and D- sugars are NOT. For example, L-arabinose []20
D=+105.1˚ and D-fructose []20D=-92
˚
-L-arabinose (pyranose form)
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How to determine L- and D-
• First, find the chiral carbon
CH- =O|
H- -OHC
H- -HC|
|OH
C
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How to determine L- and D-
• If there is more than one chiral carbon, then…
H-C
H-C-OH|
H2-C-OH
|H-C-OH
|
=OH2-C-OH
C=O
H-C-OH
H2-C-OH
HO-
|
|
|
|-HC
D- L-
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C5
Formation of the cyclic form H O
HCC
H
CH
H
CH2OH
HOOH
OH
OH
C1CH
HO
OC
H
OHCHOH
C
H
OHC HOH
CH2OH
1
5
6
anomer
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Other sugar generate 5-member ring
C5
HCC
H
CH
CH2OH
HOO
OH
OH
2
CH2OH
H
OC
OH
OHCHOH
CH
C
HOCH2
25
6
CH2OHOH
CH2OH
anomer
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(few)
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The importance of a sialic acid
a sialic acid
Normal protein Asialo-glycoprotein:Will be removed by asialoglycoprotein receptors in the liver
Sialidase(neuraminidase)
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Monosaccharides• Colorless, crystalline solids• Water soluble but not soluble in nonpolar solvent
• Taste sweet
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Monosaccharides have reducing powers
http://www.uni-regensburg.de/Fakultaeten/nat_Fak_IV/Organische_Chemie/Didaktik/Keusch/Grafik/fehling2.gif
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Disaccharide is made by joining two monosaccharides
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Lactose is only present in milk
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Sucrose is also called table sugar
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Trehalose is a major constituent of insect hemolymph
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3 ≦oligosaccharide ≦20
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Polysaccharides
Polysaccharides can serve as fuels, structural elements, and
extracellular support.
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Polysaccharides
• Homopolysaccharides– Starch (amylose, amylopectin)– Glycogen– Chitin
• Heteropolysaccharides– Peptidoglycan– Agar (agarose, agaropectin)– Glycosaminoglycans
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Starch and glycogen are polymers of -D-glucose
• The main chain of starch and glycogen are consisted of -D-glucose joined by (14) glycosidic bonds.
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The branch point of starch and glycogen : (16)
• Amylopectin and glycogen have branchs.
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Cellulose is a polymer of -D-glucose
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amylose
cellulose
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Chitin : polymer of -N-acetyl-D-glucosamine
GlcNAc
GlcNAc
GlcNAc
GlcNAc
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Peptidoglycan contains heteropolysaccharides
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Agarose is very important in molecular biology applications
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Glycosaminoglycans are heteropolysaccharides
• N-acetylglucosamine or N-acetyllgalactosamine + uronic acid (D-glucuronic or L-iduronic acid)
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Heparin is a natural anticoagulant
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Glycoconjugates• Proteoglycans – glycosaminoglycan chains covalently joined to a membrane or secreted protein
• Glycoproteins – complex oligosaccharides covalently joined to a protein
• Glycolipids – membrane lipids with oligosaccharides as hydrophilic head
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Proteoglycans
Point of attachment
Site of attachment
Trisaccharide bridge
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Proteoglycan aggregates
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Glycoproteins• Glycoproteins are carbohydrate-protein conjugates in which the carbohydrate moieties are smaller and more structurally diverse than the glycosaminoglycans of proteoglycans.
• Anomeric carbon of carbohydrate + -OH of Ser/Thr or –NH2 of Asn
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Glycophorin A• Glycophorin A has 16 oligosaccharides covalently attached to it, with total 60 to 70 monosaccharide residues.
• It is the MN antigen of human erythrocytes.
Ser1, Gly5 M
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O- and N-linked glycosidic linkages
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Glycolipid and lipopolysaccharides are membrane components
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Glycobiology
Carbohydrates can be served as informational
molecules
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Sugar serves as “aging” marker of proteins
a sialic acid
Normal protein Asialo-glycoprotein:Will be removed by asialoglycoprotein receptors in the liver
Sialidase(neuraminidase)
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Lectins• Lectins are proteins that bind carbohydrates with high affinity and specificity.
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Membrane lectins of H. pylori binds to membrane glycoprotein of gastric epithelial cell Membrane lectins (P-, E- and
L-selectins) play important role in the movement of immune cells