| Popis: |
The synthesis of the epimeric 6- C -phenylglucoses is reported; these are the first compounds with one of the prochiral methylene hydrogens on C-6 of a hexose being replaced by an aryl group. Both isomers inhibit glucokinase and provide further indications that 6- C -alkyl- and 6- C -aryl-carbohydrates may provide a new range of sugar mimics that control enzymes associated with formation, hydrolysis and other fates of sugar-6-phosphates. X-ray crystal structures of 6-C- phenyl- l -glycero-β- d -gluco- hexopyranose and (2 R ,3 S ,4 R ,6 R ,7 R ,8 S )2,3,6,7-tetrahydroxy-6,7-O-isopropylidene-1,5-oxa-2-phenyl-bicyclo-[3.3.0]octane are reported. |
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