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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

6-Deoxyheptoses in Nature, Chemistry, and Medicine

Author(s): Zbigniew Pakulski, Frederic Poly, Nelum Dorabawila, Patricia Guerry and Mario A. Monteiro

Volume 18, Issue 14, 2014

Page: [1818 - 1845] Pages: 28

DOI: 10.2174/1385272819666140527231937

Price: $65

Abstract

6-Deoxyheptoses are rare higher-carbon sugars isolated from lipopolysaccharides (LPS) and capsular polysaccharides (CPS) of some Gram-negative bacteria (Campylobacter, Yersinia, Burkholderia, Eubacterium, Plesiomonas, and Escherichia species). They occur in numerous structural variations of the bacterial polysaccharides (PS), which are briefly summarized. Biochemical pathways involving deoxygenation of heptoses as well as possible approaches towards the chemical synthesis of these unusual monosaccharides will be discussed. The most important methods for the preparation of 6-deoxyheptoses include elongation of pentose or hexose chains by nucleophilic substitution, Wittig-type reaction, and nucleophilic addition into carbonyl group.

Keywords: 6-deoxyheptose, biosynthesis, synthesis, Burkholderia, Campylobacter, Yersinia.


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