Synthesis of Bradyrhizose Oligosaccharides Relevant to the Bradyrhizobium O‐Antigen. Issue 8 (18th January 2017)

• Record Type: Journal Article
• Authors: Li, Wei; Silipo, Alba; Gersby, Lotte Bettina Andersen; Newman, Mari‐Anne; Molinaro, Antonio; Yu, Biao
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 8(2017)
• Page Start: 2092
• Page End: 2096
• Publication Date: 2017-01-18
• Subjects: bradyrhizobium -- carbohydrates -- conformation -- glycosylation -- oligosaccharides; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201610680
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The unique α‐(1→7)‐bradyrhizoside linkages are constructed for the first time via judicious choice of the glycosylation partners and conditions, thus tetra‐ and penta‐bradyrhizosides relevant to the peculiar O‐antigen of Bradyrhizobium are synthesized, which are shown to adopt the defined right‐handed helical conformations and to be unable to induce innate immune responses in plants. Abstract : Sugars behind nitrogen fixation : Oligomers of the inositol‐fused monosaccharide bradyrhizose were constructed via unique α‐(1→7)‐linkages through the judicious choice of glycosylation partners and conditions. The oligomers form precise 3D structures and, unlike other pathogenic O‐antigen oligosaccharides, they are unable to induce innate immune responses in Arabidopsis.