Issue 32, 2015
From the journal:

Chemical Communications

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

Wei Li,a   Alba Silipo,b   Antonio Molinaro*b  and  Biao Yu*a  

* Corresponding authors

a State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: byu@mail.sioc.ac.cn

b Department of Chemical Sciences, University of Naples “Federico II”, Via Cintia 4, 80126 Napoli, Italy
E-mail: molinaro@unina.it

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

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Article information

DOI
https://doi.org/10.1039/C5CC00752F
Article type
Communication
Submitted
27 Jan 2015
Accepted
14 Mar 2015
First published
16 Mar 2015

Chem. Commun., 2015,51, 6964-6967

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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

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