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A drug targeting motif for glycosidase inhibitors: an iminosugar–boronate shows unexpectedly selective β-galactosidase inhibition

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
49
Identifiers
DOI: 10.1016/s0040-4039(02)02196-2
Disciplines
  • Biology

Abstract

Abstract Boronic acids were tethered to iminosugars in compounds such as 8 and 13 in order to increase their affinity for cell surfaces where glycoprotein processing enzymes are operative. Surprisingly, this modification diminished α-mannosidase inhibition while increasing β-galactosidase inhibitory activity ( 8 : K i =2.0×10 −4 M versus E. coli β-galactosidase). The presence of a boronate in 8 and 13 has a profound impact on the specificity of this inhibition.

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