Synthesis of 1,2,3-triazole-linked glycohybrids in the gluco-, gulo-, and allopyranose series

被引：5
|
作者：
Uzulena, Jevgenija [1 ]
Rjabovs, Vitalijs [1 ]
Moreno-Vargas, Antonio J. [2 ]
Turks, Maris [1 ]
机构：
[1] Riga Tech Univ, Inst Technol Organ Chem, LV-1048 Riga, Latvia
[2] Univ Seville, Fac Chem, Dept Organ Chem, E-41002 Seville, Spain
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 51卷 / 07期
关键词：
allose; glucose; gulose; 1,2,3-triazole; click chemistry; extended bistriazolyl linker; furanose-pyranose equilibrium; galactosidase activators; BIOLOGICAL-ACTIVITY; TERMINAL ALKYNES; CLICK REACTION; DERIVATIVES; INHIBITORS; CHEMISTRY; TRIAZOLE; AZIDES; TRANSFORMATIONS; ACTIVATORS;
D O I：
10.1007/s10593-015-1754-x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ketone derived from diacetone-alpha-D-glucose is a suitable starting material for the synthesis of 3-C-linked glycohybrids containing 1,2,3-triazole moiety as an intersugar linkage. The pyranose tautomers of 3-deoxy-3-(1,2,3-1H-triazol-1-yl) glucose, 3-C-[(1,2,3-1H-triazol-1-yl) methyl] allose and 3-C-[(1,2,3-1H-triazol-1-yl) methyl] gulose moieties are released upon the acidic hydrolysis of the corresponding O-isopropylidene-protected furanosyl-type synthetic intermediates. Some of the title compounds show a rare property of activating beta-galactosidase from Escherichia coli.
引用
收藏
页码：664 / 671
页数：8
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