Synthesis, structure and enzymatic evaluation of new spiro oxathiazole sugar derivatives

Jean Pierre Praly, René Faure, Benoît Joseph, Laszlo Kiss, Patrick Rollin

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

On treatment with N-bromosuccinimide under irradiation in refluxing carbon tetrachloride, 2,3,4,6-tetra-O-acetyl-1-S-(Z)-benzhydroximoyl-1-thio-D-glucopyranose 1 and various analogs yielded new spiro anomericoxathiazole derivatives in ≈60% total yield. After deacetylation, the tested major 1(S) epimers were found good competitive inhibitors of emulsin β-D-glucosidase whereas a 1 (R) counterpart had no effect on the enzyme.

Original languageEnglish
Pages (from-to)6559-6568
Number of pages10
JournalTetrahedron
Volume50
Issue number22
DOIs
Publication statusPublished - 1994

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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