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Syntheses and properties of some photolabile β-thioglycosides. Potential photoaffinity reagents for β-glycoside hydrolases

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
46
Issue
9
Identifiers
DOI: 10.1016/s0040-4020(01)85452-1
Disciplines
  • Chemistry

Abstract

Abstract 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.

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