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Lecture 9

lecture 9 stereochemistry

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Stavroula Andreopoulos

Lecture 9 Stereochemistry - aldoses with at least three carbons and ketoses with at least four carbons contain chiral centers - each have a specific configuration about each asymmetric center - Fischer projection – drawings used to specify the configurations - prefixes D and L refer to the configuration of the highest numbered asymmetric carbon – for monosaccharides with two or more asymmetric carbons - configuration D – if the hydroxyl group on the highest numbered asymmetric carbon is to the right in a Fischer projection - configurations D and L do not specify the sign of rotation of plane-polarized light - optical rotation is specified by a + or – sign along with the D and L configurations - example: D(+)-glucose is dextrorotatory and D-fructose (D(-)-fructose) is levorotatory - most monosaccharides are in D-form in nature (L-form with amino acids) - enantiomer – D- and L- forms are mirror images of each other – with molecules with two or more chiral centers - diastereomer – pairs of isomers that have opposite configurations but are not mirror images - epimer – two sugars that differ in configuration at only one chiral center Cycli
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