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Unformatted text preview: CHO H OH CH 2 OH H OH The configurational atom of a carbohydrate is the stereocenter farthest from the aldehyde. (the highest numbered stereocenter) In D-sugars this stereocenter is R, In L-sugars this stereocenter is S. D-erythrose L-erythrose D-threose L-threose Configurational atom CHO HO H CH 2 OH H OH CHO HO H CH 2 OH HO H CHO H OH CH 2 OH HO H D-aldotetroses L-aldotetroses NOTE: D and L sugars with the same name are ENANTIOMERS D-erythrose is 2R, 3R and L- erythrose is 2S, 3S (R) (R) (S) (S) Aldohexoses D-glucose L-glucose D-idose L-idose CHO H OH HO H H OH H OH CH 2 OH CHO HO H H OH HO H HO H CH 2 OH CHO HO H H OH HO H H OH CH 2 OH CHO H OH HO H H OH HO H CH 2 OH enantiomers C3-epimers Epimers: diastereomers with one unique stereocenter (all stereocenters are the same except one) D-allose CHO H OH H OH H OH H OH CH 2 OH enantiomers -D-glucopyranose H OH HO H H OH H O CH 2 OH -D-glucopyranose - D-glucofuranose -L-glucofuranose OH H H OH HO H H OH H O CH 2 OH H HO OH at anomeric carbon and oxygen attached to the configurational atom are on the same side in Fischer projection OH at anomeric caron and oxygen attached to the configurational atom are on opposite sides in Fischer projection...
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This note was uploaded on 04/02/2008 for the course CHEM 215 taught by Professor Koreeda during the Winter '07 term at University of Michigan.
- Winter '07