Carbohydrates_sugar_coated

Carbohydrates_sugar_coated - The Sweet life Carbohydrates...

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The Sweet life arbohydrates Carbohydrates
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arbohydrates Carbohydrates opics Topics monosaccharides stereochemistry and structure glycosidic bonds other derivatives ligosaccharides oligosaccharides disaccharides
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polysaccharides: storage polysaccharides: starch and glycogen structural polysaccharides: cellulose and chitin glycoproteins glycolipids
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onosaccharides Monosaccharides olyhydroxy aldehydes : aldoses Polyhydroxy aldehydes : aldoses Polyhydroxy ketones: ketoses 3-7 carbon atoms (triose heptoses) ereochemistry based on the stereochemistry based on the stereochemistry elucidated by Emil ischer D- nd L- Fischer, D and L
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Glyceraldehyde and dihydroxyacetone re the simplest sugars (trioses) are the simplest sugars (trioses)
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D-or L- designation determined by stereochemistry at last asymmetric carbon any stereocenters any isomers many stereocenters many isomers enantiomers: mirror images epimers: differ at only one stereocenter diastereomers: differ at more than one site
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Examples of an aldose, a ketose and two nantiomers enantiomers
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Examples of epimers and enantiomers epimers
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Families of D-aldoses aldohexoses
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addition of one carbon adds a stereocenter - etoses D Ketoses
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Linear sugar structures spontaneously cyclize: (secondary) O H CH 2 R alcohol R C H 2 OH + R 1 H aldehyde R 1 C O H O C H 2 R R 1 C O H O C H 2 R alcohol hemiacetal O O H acetal O H 2 C R R C H 2 OH + R 1 R 2 alcohol ketone R 1 C R 2 O C H 2 R R 1 C R 2 O C H 2 R alcohol hemiketal ketal Sugars are actually linked forms of an gy aldehyde/ketone and an alcohol
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C O 1 OH 2 HO 3 OH 4 O H 5 CH 2 OH 6
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C O H O CH OH 2
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C C O H 2 OH O OH
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CH 2 OH C O H O H O OH OH
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CH 2 OH C O H O H O OH OH
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CH 2 OH C H O O O OH OH
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CH 2 OH C H O O H O OH α OH
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CH 2 OH C H O O H O OH OH
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CH 2 OH C H O O O OH OH
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CH 2 OH C O H O H O OH OH
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CH 2 OH C O H O H O OH OH
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CH 2 OH C H O O O OH OH
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CH 2 OH C O H H O β O OH OH
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CH 2 OH 6 C H O 5 O H O OH 1 2 4 OH 3
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Cyclic forms of monosaccharides carbons and larger: form a cyclic structure 5 carbons and larger form a cyclic structure Cyclized structures are called furanoses (5- membered ring) and pyranoses (6-membered ring)
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The carbon attached to the ring oxygen and the hydroxyl oxygen is called the “anomeric carbon” Note that the anomeric Carbon has two bonds to oxygen and all the others have only one bond to oxygen
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http://www.stolaf.edu/people/giannini/flashanimat/carbohydrates/glucose.swf
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Which conformations are most common?
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H OH H O HO H H H O H H H H H a-anomer b-anomer -anomer β -anomer Two possibilities for the aldehyde/ketone carbon when cyclized: up or down β -anomer: OH in the equatorial position (up)same as CH OH 2 α -anomer: OH is in the axial position (down) opposite to CH 2 OH
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This note was uploaded on 07/07/2010 for the course BIOL 237 taught by Professor Daragilbert during the Fall '09 term at Waterloo.

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Carbohydrates_sugar_coated - The Sweet life Carbohydrates...

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