Evaluation of C-(β-D-galactosyl) and C-(2-deoxy-D-lyxo-hex-1-enopyranosyl) (D-galactal type) derivatives as inhibitors of β-D-galactosidase from Escherichia coli

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

C-(2-Deoxy-D-lyxo-hex-1-enopyranosyl)formamide was prepared from acetylated C-(β-D-galactopyranosyl)formamide by a radical-mediated bromination-zinc/N-methylimidazole-induced reductive elimination-Zemplen deacetylation reaction sequence. The preparation of acetylated 5-(2-deoxy-D-lyxo-hex-1-enopyranosyl)tetrazole was improved. Methyl C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formimidate was transformed by benzylamine into N-benzyl-C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formamidine and, after hydrolysis to methyl C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formate, into N-benzyl-C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formamide. A series of C-(β-D-galactopyranosyl) and C-(2-deoxy-D-lyxo-hex-1-enopyranosyl) derivatives was comparatively investigated for E. coli β-D-galactosidase inhibitory activity. N-Benzyl-C-(2-deoxy-D-lyxohex-1-enopyranosyl)formamidine was the best inhibitor and had K(i)=6 μM (on the basis of its free base concentration, K(i)=8.3 nM was obtained). Basicity and hydrophobicity of the aglycon proved to be more important factors for the inhibition than the conformation of the sugar ring.

Original languageEnglish
Pages (from-to)43-52
Number of pages10
JournalCarbohydrate Research
Volume291
DOIs
Publication statusPublished - Sep 23 1996

Keywords

  • C-glycosides
  • D-galactal derivatives
  • E. coli β-D-galactosidase
  • enzyme inhibition
  • radical-mediated bromination
  • reductive elimination
  • zinc/N-methylimidazole reagent

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Evaluation of C-(β-D-galactosyl) and C-(2-deoxy-D-lyxo-hex-1-enopyranosyl) (D-galactal type) derivatives as inhibitors of β-D-galactosidase from Escherichia coli'. Together they form a unique fingerprint.

  • Cite this