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Principles of Biochemistry (Carbohydrates)

Principles of Biochemistry (Carbohydrates)

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Published by Sohaib Nazir
Principles of Biochemistry (Carbohydrates)
Principles of Biochemistry (Carbohydrates)

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Published by: Sohaib Nazir on Jul 25, 2013
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02/01/2015

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Carbohydrates

Structure & Function of Biomolecules

Carbohydrates

Most abundant biomolecule Many functions

 

Energy/energy storage Structural elements Mediator of interactions

Monosaccharides
 

Simple sugars Polyhydroxy aldehydes or ketones

Monosaccharides  General formula: (CH2O)n  n=3-7 Most highly oxidized carbon at top (C1) .

Important Monosaccharides H OH H HO HO H H OH H OH OH OH HO O O HO OH H HO H H O OH OH H HO OH H Glucose Fructose Galactose Must be able to draw Fischer projections and Haworth projections of these. .

Stereoisomers H  van’t Hoff’s rule  # of stereoisomers = where n = # of assymmetric carbons. 2n H HO H H C C C C C O OH H OH OH  n=4 # stereoisomers = 16  CH2OH .

Types of Stereoisomers  Enantiomers  Mirror images   Diastereomers Not mirror images  Epimers  Differ at a single chiral carbon .

Examples H C H HO H H C C C C O OH H OH OH HO H HO HO H C C C C C O H OH H H H H H H H C C C C C O OH OH OH OH HO HO HO H H C C C C C O H H H OH CH2OH CH2OH CH2OH CH2OH D-glucose L-glucose (enantiomer) D-allose (epimer at C3) D-talose (diastereomer) .

then D configuration H OH on left. H C H HO H C C C C O OH H OH OH HO H HO HO H C C C C C O H OH H H OH on right. then L configuration CH2OH CH2OH D-glucose L-glucose .Configuration  Look at chiral carbon farthest from carbonyl carbon to determine D or L configuration.

Reactions with Alcohols .

Cyclization H H HO H H C C C C C O OH H OH OH H H HO H H C C C C C CH2OH OH OH O H OH CH2OH .

Furanoses/Pyranoses O O Furan Pyran .

Haworth Projections Anomers .

Proportion of each anomer differs for each sugar.  .Mutarotation  a and b forms spontaneously interconvert in an aqueous environment.

then the sugar is a reducing sugar.Reducing Sugars  Sugars that are susceptible to oxidation. If a free OH is present. (reducing)  Look at C1 on aldoses or C2 on ketoses. (not reducing) .

Oxidation Reactions Oxidation of aldehyde = aldonic acid OH C O OH H OH OH O H HO H H C C C C C C OH O OH H OH OH O Oxidation of terminal CH2OH = uronic acid H Oxidation of both = aldaric acid OH C H HO H H C C C C O H C C C C C OH HO H H OH H OH CH2OH OH D-Gluconic acid D-Glucuronic acid D-Glucaric acid .

Reduction Reactions OH CH2OH C H HO H H C C C C O H OH C C C C OH H OH OH H2 H OH OH HO H H Catalyst CH2OH CH2OH D-Glucose D-Glucitol (Sorbitol) Sugar alcohol .

Important in carbohydrate metabolism. .Isomerization Generally enzyme catalyzed reactions.

Modifications of Monosaccharides O-O P H O O CH2OH H O OH H OH H OH O HO HO H OH N-acetyl-a-D-glucosamine b-D-Glucose-6-phosphate 2-deoxy-b-D-ribose .

Glycosidic Linkages .

Glycosidic Linkages Glycosidic linkage Aglycone .

Disaccharides  Bond type   Look at first subunit to determine if a or b Number according to 1st subunit then 2nd subunit CH2OH a 1-4 linkage O CH2OH O OH OH OH OH O OH OH Maltose (a-D glucose (a 1-4) b-D glucose) .

a-D glucose (a 1-2) b-D fructose .Sucrose (must be able to draw)  Table sugar  Is sucrose a reducing sugar?  No. because glycosidic linkage joins the 2 anomeric carbons.

respectively. N-linked   Attached via asparagine.  O-linked  Attached via threonine or serine or OH on lipid .Oligosaccharides   3 .10 or more subunits Often attached to proteins or lipids to form glycoproteins or glycolipids.

Homopolysaccharides or heteropolysaccharides .Polysaccharides   Composed of many subunits.

 Branches occur ~12-25 residues & contain ~20-25 glucoses  Use a amylase to digest. .Storage Polysaccharides: Plants  Starch  Glucose monomers  Two forms  Amylose  Unbranched a1-4 linkages  Amylopectin  a1-4 backbone with a1-6 branches.

Glycogen phosphorylase breaks a1-4 linkages. Debranching enzyme breaks a1-6 linkages. a1-4 backbone with a1-6 branches.     .Storage Polysaccharides: Animals  Glycogen  Stored in liver & in muscles. Branches occur ~10 residues & contain ~ 812 glucoses.

Framework of Nucleic Acids Deoxyribose (DNA) Ribose (RNA) .

Mammals lack cellulose degrading enzyme.  Found in plant cell wall.Structural Elements: Plants  Cellulose Homopolysaccharide   Glucose subunits joined by b1-4 linkages.  .

 Makes up exoskeleton of arthropods and cell wall of some fungi .Structural Elements: Arthropods and Some Fungi   Chitin Homopolysaccharide  N-acetylglucosamine monomers joined by b1-4 linkages.

 . Bind a lot of H2O.Structural Elements: Animals  Glycosaminoglycans (GAGs)  Heteropolysaccharides  Disaccharide repeating units  Negatively charged at physiological pH.

jpg .Cell-Cell Recognition: Blood Group Antigens Carbohydrate portion of blood group glycolipids http://oregonstate.edu/instruction/bb450/stryer/ch11/Slide56.

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