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A new approach to the synthesis of legionaminic acid analogues.

ABSTRACT: 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.

SUBMITTER: Carter JR

PROVIDER: S-EPMC9088180 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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A new approach to the synthesis of legionaminic acid analogues.

Carter James R JR Kiefel Milton J MJ

RSC advances 20181019 62

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 ame ...[more]

PMID: 35547932

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