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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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Detalles Bibliográficos
Autores principales: Carter, James R., Kiefel, Milton J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9088180/
https://www.ncbi.nlm.nih.gov/pubmed/35547932
http://dx.doi.org/10.1039/c8ra07771a
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author Carter, James R.
Kiefel, Milton J.
author_facet Carter, James R.
Kiefel, Milton J.
author_sort Carter, James R.
collection PubMed
description 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.
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spelling pubmed-90881802022-05-10 A new approach to the synthesis of legionaminic acid analogues Carter, James R. Kiefel, Milton J. RSC Adv Chemistry 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. The Royal Society of Chemistry 2018-10-19 /pmc/articles/PMC9088180/ /pubmed/35547932 http://dx.doi.org/10.1039/c8ra07771a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Carter, James R.
Kiefel, Milton J.
A new approach to the synthesis of legionaminic acid analogues
title A new approach to the synthesis of legionaminic acid analogues
title_full A new approach to the synthesis of legionaminic acid analogues
title_fullStr A new approach to the synthesis of legionaminic acid analogues
title_full_unstemmed A new approach to the synthesis of legionaminic acid analogues
title_short A new approach to the synthesis of legionaminic acid analogues
title_sort new approach to the synthesis of legionaminic acid analogues
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9088180/
https://www.ncbi.nlm.nih.gov/pubmed/35547932
http://dx.doi.org/10.1039/c8ra07771a
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