Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability

[Image: see text] Galactofurans are an important structural constituent of arabinogalactan and lipopolysaccharides (LPS) ubiquitously present on the envelopes of all Mycobacteria. Key to the automated glycan assembly (AGA) of linear galactofuranosides as long as 20-mers was the identification of thi...

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Autores principales: Sabbavarapu, Narayana Murthy, Seeberger, Peter H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8154612/
https://www.ncbi.nlm.nih.gov/pubmed/33960786
http://dx.doi.org/10.1021/acs.joc.1c00505
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author Sabbavarapu, Narayana Murthy
Seeberger, Peter H.
author_facet Sabbavarapu, Narayana Murthy
Seeberger, Peter H.
author_sort Sabbavarapu, Narayana Murthy
collection PubMed
description [Image: see text] Galactofurans are an important structural constituent of arabinogalactan and lipopolysaccharides (LPS) ubiquitously present on the envelopes of all Mycobacteria. Key to the automated glycan assembly (AGA) of linear galactofuranosides as long as 20-mers was the identification of thioglycoside building blocks with a fine balance of stereoelectronic and steric effects to ensure the stability of oligogalactofuranoside during the synthesis. A benzoylated galactofuranose thioglycoside building block proved most efficient for oligosaccharide construction.
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spelling pubmed-81546122021-05-27 Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability Sabbavarapu, Narayana Murthy Seeberger, Peter H. J Org Chem [Image: see text] Galactofurans are an important structural constituent of arabinogalactan and lipopolysaccharides (LPS) ubiquitously present on the envelopes of all Mycobacteria. Key to the automated glycan assembly (AGA) of linear galactofuranosides as long as 20-mers was the identification of thioglycoside building blocks with a fine balance of stereoelectronic and steric effects to ensure the stability of oligogalactofuranoside during the synthesis. A benzoylated galactofuranose thioglycoside building block proved most efficient for oligosaccharide construction. American Chemical Society 2021-05-07 2021-05-21 /pmc/articles/PMC8154612/ /pubmed/33960786 http://dx.doi.org/10.1021/acs.joc.1c00505 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Sabbavarapu, Narayana Murthy
Seeberger, Peter H.
Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability
title Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability
title_full Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability
title_fullStr Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability
title_full_unstemmed Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability
title_short Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability
title_sort automated glycan assembly of oligogalactofuranosides reveals the influence of protecting groups on oligosaccharide stability
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8154612/
https://www.ncbi.nlm.nih.gov/pubmed/33960786
http://dx.doi.org/10.1021/acs.joc.1c00505
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