Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor

Carla Marino, Pal Herczegh, Rosa M. De Lederkremer

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The development of β-D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because β-D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared β-D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated β-D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-β-D-Galactofuranosyl-O-ethylthiourethane, N-β-D-galactofuranosyl-4-oxoimidazolidine-2-thione, N-β-D-galactofuranosyl-4-imidazoline-2-thione, and N-β-D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo β-D-galactofuranosidase inhibitor.

Original languageEnglish
Pages (from-to)123-128
Number of pages6
JournalCarbohydrate Research
Volume333
Issue number2
DOIs
Publication statusPublished - Jul 3 2001

Keywords

  • 4-Imidazoline
  • Galactofuranosidase inhibitors
  • Imidazolidine-2-thion derivatives
  • Isothiocyanate
  • Thiohydantoin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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