Jump to main content
Jump to site search

Issue 32, 2015
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Jan 2015, accepted on 14 Mar 2015 and first published on 16 Mar 2015


Article type: Communication
DOI: 10.1039/C5CC00752F
Author version
available:
Download author version (PDF)
Citation: Chem. Commun., 2015,51, 6964-6967
  •   Request permissions

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

    W. Li, A. Silipo, A. Molinaro and B. Yu, Chem. Commun., 2015, 51, 6964
    DOI: 10.1039/C5CC00752F

Search articles by author

Spotlight

Advertisements