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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2018
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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. |
format | Online Article Text |
id | pubmed-9088180 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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