title: Synthesis of bradyrhizose, a unique inositol-fused monosaccharide relevant to a Nod-factor independent nitrogen fixation.
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.
authors: 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. byu@mail.sioc.ac.cn.
authors: Wei
authors: W
authors: Li
authors: Alba
authors: A
authors: Silipo
authors: Antonio
authors: A
authors: Molinaro
authors: Biao
authors: B
authors: Yu
mesh_terms: D020369:Bradyrhizobium / Q000737:chemistry / Q000378:metabolism; D060326:Chemistry Techniques, Synthetic; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D009586:Nitrogen Fixation
chemical_list: D006574:Heterocyclic Compounds, 2-Ring; D009005:Monosaccharides; D007294:Inositol