Synthesis of branched inner-core oligosaccharides of neisserial lipooligosaccharides

TETRAHEDRON

卷:96

Article

Ichiyanagi, Tsuyoshi¹  Narimoto, Hirofumi¹  Ohtani, Naoki¹ 

[1] Tottori Univ, Fac Agr, Tottori 6808553, Japan

关键词: Lipooligosaccharide;    Lipopolysaccharide;    Inner core;    3-deoxy-D-manno-oct-2-ulsonic acid;    L-glycero-D-mannoheptose;   

DOI  :  10.1016/j.tet.2021.132397

来源: Elsevier

【 摘 要 】

In this study, branched inner-core oligosaccharides of neisserial lipooligosaccharides was successively synthesized. We found that the glycosylation of a 4-O-substituted heptose derivative with a heptosyl donor proceeded smoothly proceeded in toluene and provided corresponding 3,4-di-O-substituted heptose as a single diastereomer. In addition, we found that the fragment condensation of a 3,4-di-Osubstituded heptosyl donor with the axially oriented 5-position of a 4-O-substituted Kdo acceptor provided a consecutive branched hexasaccharide with a vicinal trans-diol of L-glycero-D-manno-heptose (Hep) and a vicinal cis-diol of 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) in its structure. (C) 2021 Elsevier Ltd. All rights reserved.

【 授权许可】

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