A new approach to the synthesis of legionaminic acid analogues

Legionaminic acid is a member of the nonulosonic acids, which are a class of sugars considered to be a virulence factor within a wide variety of pathogenic bacteria. We have developed a synthetic pathway towards C-7 analogues of legionaminic acid starting from Neu5Ac, resulting in the complete synth...

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Bibliographic Details
Published in:RSC advances 2018-10, Vol.8 (62), p.35768-35775
Main Authors: Carter, James R, Kiefel, Milton J
Format: Article
Language:English
Subjects:
Acids
Chemistry
Sugar
Synthesis
Virulence
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Summary:Legionaminic acid is a member of the nonulosonic acids, which are a class of sugars considered to be a virulence factor within a wide variety of pathogenic bacteria. We have developed a synthetic pathway towards C-7 analogues of legionaminic acid starting from Neu5Ac, resulting in the complete synthesis of both legionaminic acid, and its C-7 epimer, from a common precurser. Our approach involves the late-stage introduction of the requisite C-7 nitrogen functionality, thus making our strategy amenable to the introduction of a range of different amide groups at C-7 of legionaminic acid. We report the synthesis of the bacterial nonulosonic acid legionaminic acid, together with its C-7 epimer, from a common precursor derived from N -acetylneuraminic acid.
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra07771a