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The first example of a 6-C-aryl-D-glucose: Inhibition of glucokinase

Abstract:

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-he...

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Publication status:
Published

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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
7
Issue:
9
Pages:
2761-2772
Publication date:
1996-09-05
DOI:
ISSN:
0957-4166
URN:
uuid:4f536bea-5c03-4eba-9879-70e974570169
Source identifiers:
45307
Local pid:
pubs:45307
Language:
English

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