Synthesis of Three C-Glycoside Analogues of UDP-Galactopyranose as Conformational Probes for the Mutase-Catalyzed Furanose/Pyranose Interconversion

被引：40
作者：
Caravano, Audrey [1 ]
Vincent, Stephane P. [1 ]
机构：
[1] Univ Namur FUNDP, Dept Chim, Chim Bioorgan Lab, B-5000 Namur, Belgium
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 11期
关键词：
Biosynthesis; Phosphorus; Inhibitors; C-Glycosides; Carbohydrates; STD-NMR SPECTROSCOPY; MYCOBACTERIUM-TUBERCULOSIS; STEREOSELECTIVE-SYNTHESIS; CHEMICAL-SYNTHESIS; EXO-GLYCALS; CELL-WALL; CARBOHYDRATE-CHEMISTRY; GALACTAN BIOSYNTHESIS; ESCHERICHIA-COLI; GAL MUTASE;
D O I：
10.1002/ejoc.200801249
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
UDP-galactopyranose mutase (UGM) catalyzes the isomerization of UDP-galactopyranose (UDP-Galp) into UDP-galactofuranose (UDP-Galf), an essential step of the mycobacterial cell wall biosynthesis. In order to probe the UGM binding pocket, we synthesized the alpha- and beta-C-glycosidic analogues of UDP-galacopyranose along with the corresponding UDP-exo-galactal. Preliminary inhibition evaluation indicated that UDP-exo-galactal inhibits UGM with a binding affinity similar to that of UDP-alpha-C-galactopyranose. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码：1771 / 1780
页数：10
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