Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a'-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.0(2,4)]nonan-9-ol: glycosidase inhibitory activity of N-substituted 5a-carba-beta-gluco- and beta-galactopyranosylamines, and derivatives thereof

Bioorg Med Chem Lett. 2004 Oct 18;14(20):5183-8. doi: 10.1016/j.bmcl.2004.07.091.

Abstract

Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2 microM, green coffee beans).

Publication types

  • Comparative Study

MeSH terms

  • Alkanes / chemistry*
  • Amino Sugars / chemical synthesis*
  • Amino Sugars / chemistry
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Galactose / chemical synthesis*
  • Galactose / chemistry
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Glycoside Hydrolases / chemistry
  • Heterocyclic Compounds, 3-Ring / chemistry*

Substances

  • Alkanes
  • Amino Sugars
  • Disaccharides
  • Heterocyclic Compounds, 3-Ring
  • Glycoside Hydrolases
  • Galactose