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

被引:18
作者
Bleriot, Y
Veighey, CR
Smelt, KH
Cadefau, J
Stalmans, W
Biggadike, K
Lane, AL
Muller, M
Watkin, DJ
Fleet, GWJ
机构
[1] UNIV OXFORD,OXFORD CTR MOL SCI,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
[2] CATHOLIC UNIV LEUVEN,FAC GENEESKUNDE,AFDELING BIOCHEM,B-3000 LOUVAIN,BELGIUM
[3] GLAXO WELLCOME RES & DEV LTD,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND
[4] CHEM CRYSTALLOG LAB,OXFORD OX1 3QU,ENGLAND
关键词
D O I
10.1016/0957-4166(96)00356-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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 of 6-C-phenyl-L-glycero-beta-D-gluco-hexopyranose and (2R,3S,4R,6R,7R,8S)2,3,6,7-tetrahydroxy-6,7-O-isopropylidene-1,5-oxa-2-phenyl-bicyclo-[3.3.0]octane are reported. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2761 / 2772
页数:12
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