02stereo - I.A.ii.-1 Carbohydrate Stereochemistry...

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I.A.ii.-1 Carbohydrate Carbohydrate Stereochemistry Stereochemistry Sugars are generally chiral Cyclic form likewise contains stereocenters OH H OH H OH H H HO C C C C C C its mirror image is an "optical isomer" e.g. glucose H 2 OH H O e.g. at C2 carbon: This structure has a non- superimposable mirror image CHO (CHOH) 3 CH 2 OH OH H C2 4 stereocenters
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I.A.ii.-2 Defnitions Defnitions A stereoisomer diFFers in the 3-D orientation oF atoms alike in the way atoms are joined to other atoms An enantiomer is a mirror image oF the original molecule A diastereomer is an isomer with confguration changes around some but not all stereocenters not a mirror image An anomer is one oF a special pair oF diastereomeric aldoses or ketoses diFFer only in confguration about the carbonyl carbon (C1 For aldoses and C2 For ketoses) An epimer is one oF a special pair oF diastereomeric aldoses or ketoses diFFer in confguration about one carbon only
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I.A.ii.-3 Nomenclature Nomenclature Identity of sugars largely determined by their stereo- chemical conFguration Monosaccharides designated “D” or “L” by conFgura- tion of last stereogenic carbon This is the D conFguration (i.e. D-glucose) Most natural sugars have the D conFguration H H 2 OH
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This note was uploaded on 11/03/2010 for the course FST 100A taught by Professor Dungan during the Fall '08 term at UC Davis.

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02stereo - I.A.ii.-1 Carbohydrate Stereochemistry...

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