Synthesis of bradyrhizose, a unique inositol-fused monosaccharide relevant to a Nod-factor independent nitrogen fixation

Chem Commun (Camb). 2015 Apr 25;51(32):6964-7. doi: 10.1039/c5cc00752f. Epub 2015 Mar 23.

Abstract

The symbiosis of Bradyrhizobium sp. BTAi1 with its host plant Aeschynomene indica relies on a Nod-factor independent mechanism, wherein the Bradyrhizobium O-antigen is regarded as a key factor. This O-antigen polysaccharide is composed of a unique C10 monosaccharide, namely bradyrhizose, which has a galactose-inositol trans-fused scaffold, via a homogeneous α-(1 → 7)-linkage. Herein, we report the first synthesis of bradyrhizose. The scalable synthesis requires 26 steps in a high overall yield of 9%, with the inositol scaffold being constructed effectively via a Ferrier II rearrangement from a fully functionalized C2 and C4 branched pyranose derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bradyrhizobium / chemistry
  • Bradyrhizobium / metabolism
  • Chemistry Techniques, Synthetic
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemistry*
  • Heterocyclic Compounds, 2-Ring / metabolism
  • Inositol / analogs & derivatives*
  • Inositol / chemical synthesis
  • Inositol / chemistry*
  • Inositol / metabolism
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry*
  • Monosaccharides / metabolism
  • Nitrogen Fixation*

Substances

  • Heterocyclic Compounds, 2-Ring
  • Monosaccharides
  • Inositol