SYNTHESES AND PROPERTIES OF SOME PHOTOLABILE BETA-THIOGLYCOSIDES - POTENTIAL PHOTOAFFINITY REAGENTS FOR BETA-GLYCOSIDE HYDROLASES

被引：35

作者：

KUHN, CS ^{[1
]}

LEHMANN, J ^{[1
]}

STECK, J ^{[1
]}

机构：

[1] UNIV FREIBURG,INST ORGAN CHEM & BIOCHEM,ALBERTSTR 21,W-7800 FREIBURG,GERMANY

来源：

TETRAHEDRON | 1990年 / 46卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)85452-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tosyloxy-3-azi-butane, -4-azi-pentane and chloroacetone were condensed with β-D- thiosugars to yield β-D-thioglycosides which either already had a photolabile diazirino group or they had an oxo group, which could be converted into such. All photolabile β-thio-glycosides are excellent competitive inhibitors for their corresponding glycoside hydrolases (β-D-galactosidase and β-D-glucosidase). Photolysis of the glycosides in aqueous solution preferentially gave insertion products, indicating that all of the compounds were potential affinity labels. 2-Azi-propyl β-D-thio-galactoside underwent partial photochemically induced glycoside hydrolysis. © 1990.

引用

页码：3129 / 3134

页数：6

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