Cargando…

Recent Advances in Chemical Synthesis of Amino Sugars

Amino sugars are a kind of carbohydrates with one or more hydroxyl groups replaced by an amino group. They play crucial roles in a broad range of biological activities. Over the past few decades, there have been continuing efforts on the stereoselective glycosylation of amino sugars. However, the in...

Descripción completa

Detalles Bibliográficos
Autores principales: Yang, Jian, Xie, Demeng, Ma, Xiaofeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10305009/
https://www.ncbi.nlm.nih.gov/pubmed/37375279
http://dx.doi.org/10.3390/molecules28124724
_version_ 1785065633295106048
author Yang, Jian
Xie, Demeng
Ma, Xiaofeng
author_facet Yang, Jian
Xie, Demeng
Ma, Xiaofeng
author_sort Yang, Jian
collection PubMed
description Amino sugars are a kind of carbohydrates with one or more hydroxyl groups replaced by an amino group. They play crucial roles in a broad range of biological activities. Over the past few decades, there have been continuing efforts on the stereoselective glycosylation of amino sugars. However, the introduction of glycoside bearing basic nitrogen is challenging using conventional Lewis acid-promoted pathways owing to competitive coordination of the amine to the Lewis acid promoter. Additionally, diastereomeric mixtures of O-glycoside are often produced if aminoglycoside lack a C2 substituent. This review focuses on the updated overview of the way to stereoselective synthesis of 1,2-cis-aminoglycoside. The scope, mechanism, and the applications in the synthesis of complex glycoconjugates for the representative methodologies were also included.
format Online
Article
Text
id pubmed-10305009
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-103050092023-06-29 Recent Advances in Chemical Synthesis of Amino Sugars Yang, Jian Xie, Demeng Ma, Xiaofeng Molecules Review Amino sugars are a kind of carbohydrates with one or more hydroxyl groups replaced by an amino group. They play crucial roles in a broad range of biological activities. Over the past few decades, there have been continuing efforts on the stereoselective glycosylation of amino sugars. However, the introduction of glycoside bearing basic nitrogen is challenging using conventional Lewis acid-promoted pathways owing to competitive coordination of the amine to the Lewis acid promoter. Additionally, diastereomeric mixtures of O-glycoside are often produced if aminoglycoside lack a C2 substituent. This review focuses on the updated overview of the way to stereoselective synthesis of 1,2-cis-aminoglycoside. The scope, mechanism, and the applications in the synthesis of complex glycoconjugates for the representative methodologies were also included. MDPI 2023-06-12 /pmc/articles/PMC10305009/ /pubmed/37375279 http://dx.doi.org/10.3390/molecules28124724 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Yang, Jian
Xie, Demeng
Ma, Xiaofeng
Recent Advances in Chemical Synthesis of Amino Sugars
title Recent Advances in Chemical Synthesis of Amino Sugars
title_full Recent Advances in Chemical Synthesis of Amino Sugars
title_fullStr Recent Advances in Chemical Synthesis of Amino Sugars
title_full_unstemmed Recent Advances in Chemical Synthesis of Amino Sugars
title_short Recent Advances in Chemical Synthesis of Amino Sugars
title_sort recent advances in chemical synthesis of amino sugars
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10305009/
https://www.ncbi.nlm.nih.gov/pubmed/37375279
http://dx.doi.org/10.3390/molecules28124724
work_keys_str_mv AT yangjian recentadvancesinchemicalsynthesisofaminosugars
AT xiedemeng recentadvancesinchemicalsynthesisofaminosugars
AT maxiaofeng recentadvancesinchemicalsynthesisofaminosugars