Highly diastereoselective construction of L-heptosides by a sequential grignard addition/fleming-tamao oxidation

Maxime Durka, Kevin Buffet, Tianlei Li, Abdellatif Tikad, Bas Hagen, Stéphane P. Vincent

Research output: Contribution in Book/Catalog/Report/Conference proceedingChapter

Abstract

Lipopolysaccharide (LPS) is a key component of the outer membrane of Gramnegative bacteria. This complex molecule plays key roles in the mortality of many infectious diseases as well as in the virulence of numerous human pathogens. LPS consists of three main substructures: lipid A, the oligosaccharide core, and the O-antigen. The oligosaccharide core unit can itself be divided into two parts: the inner core which is formed by at least one molecule of 3-deoxy-α-D-mannooct- 2-ulopyranosonic acid (Kdo) and two molecules of l-glycero-α-D-mannoheptopyranose (l-heptose), and the outer core which is composed of hexoses. The synthesis of heptosides has thus attracted much attention for the synthetic construction of bacterial oligosaccharides, for the preparation of immunogenic glycoconjugates and for the development of novel antibacterial agents.

Original languageEnglish
Title of host publicationCarbohydrate Chemistry
Subtitle of host publicationProven Synthetic Methods
EditorsGijsbert Van der Marel, Jeroen Codee
PublisherCRC Press
Chapter11
Pages77-83
Number of pages7
Volume2
ISBN (Electronic)9780429064487
ISBN (Print)9781439875940
DOIs
Publication statusPublished - 4 Mar 2014

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    Durka, M., Buffet, K., Li, T., Tikad, A., Hagen, B., & Vincent, S. P. (2014). Highly diastereoselective construction of L-heptosides by a sequential grignard addition/fleming-tamao oxidation. In G. Van der Marel, & J. Codee (Eds.), Carbohydrate Chemistry: Proven Synthetic Methods (Vol. 2, pp. 77-83). CRC Press. https://doi.org/10.1201/b16602