Candida albicans β-1,2 mannosyl transferase Bmt3: Preparation and evaluation of a β (1,2), α (1,2)-tetramannosyl fluorescent substrate

Bioorg Med Chem. 2016 Mar 15;24(6):1362-8. doi: 10.1016/j.bmc.2016.02.008. Epub 2016 Feb 6.

Abstract

We describe for the first time the chemical synthesis of a tetramannoside, containing both α (1→2) and β (1→2) linkages. Dodecylthio (lauryl) glycosides were prepared from odorless dodecyl thiol and used as donors for the glycosylation steps. This tetramannoside, was coupled to a mantyl group, and revealed to be a perfect substrate of β-mannosyltransferase Bmt3, confirming the proposed specificity and allowing the preparation of a pentamannoside sequence (β Man (1,2) β Man (1,2) α Man (1,2) α Man (1,2) α Man) usable as a novel substrate for further elongation studies.

Keywords: Beta mannosides; Fluorescent substrate; Glycosylation; Lauryl glycoside; Mannosyl transferases; Mantyl.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Candida albicans / enzymology*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism*
  • Mannosides / chemistry
  • Mannosides / metabolism*
  • Mannosyltransferases / metabolism*
  • Molecular Conformation
  • Substrate Specificity

Substances

  • Fluorescent Dyes
  • Mannosides
  • Mannosyltransferases