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Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly

Automated chemical oligosaccharide synthesis is an attractive concept that has been successfully applied to a large number of target structures, but requires excess quantities of suitably protected and activated building blocks. Herein we demonstrate the use of biocatalysis to supply such reagents f...

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Autores principales: Marchesi, Andrea, Parmeggiani, Fabio, Louçano, João, Mattey, Ashley P., Huang, Kun, Gupta, Tanistha, Salwiczek, Mario, Flitsch, Sabine L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756758/
https://www.ncbi.nlm.nih.gov/pubmed/32857448
http://dx.doi.org/10.1002/anie.202008067
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author Marchesi, Andrea
Parmeggiani, Fabio
Louçano, João
Mattey, Ashley P.
Huang, Kun
Gupta, Tanistha
Salwiczek, Mario
Flitsch, Sabine L.
author_facet Marchesi, Andrea
Parmeggiani, Fabio
Louçano, João
Mattey, Ashley P.
Huang, Kun
Gupta, Tanistha
Salwiczek, Mario
Flitsch, Sabine L.
author_sort Marchesi, Andrea
collection PubMed
description Automated chemical oligosaccharide synthesis is an attractive concept that has been successfully applied to a large number of target structures, but requires excess quantities of suitably protected and activated building blocks. Herein we demonstrate the use of biocatalysis to supply such reagents for automated synthesis. By using the promiscuous NmLgtB‐B β1‐4 galactosyltransferase from Neisseria meningitidis we demonstrate fast and robust access to the LacNAc motif, common to many cell‐surface glycans, starting from either lactose or sucrose as glycosyl donors. The enzymatic product was shown to be successfully incorporated as a complete unit into a tetrasaccharide target by automated assembly.
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spelling pubmed-77567582020-12-28 Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly Marchesi, Andrea Parmeggiani, Fabio Louçano, João Mattey, Ashley P. Huang, Kun Gupta, Tanistha Salwiczek, Mario Flitsch, Sabine L. Angew Chem Int Ed Engl Communications Automated chemical oligosaccharide synthesis is an attractive concept that has been successfully applied to a large number of target structures, but requires excess quantities of suitably protected and activated building blocks. Herein we demonstrate the use of biocatalysis to supply such reagents for automated synthesis. By using the promiscuous NmLgtB‐B β1‐4 galactosyltransferase from Neisseria meningitidis we demonstrate fast and robust access to the LacNAc motif, common to many cell‐surface glycans, starting from either lactose or sucrose as glycosyl donors. The enzymatic product was shown to be successfully incorporated as a complete unit into a tetrasaccharide target by automated assembly. John Wiley and Sons Inc. 2020-10-02 2020-12-07 /pmc/articles/PMC7756758/ /pubmed/32857448 http://dx.doi.org/10.1002/anie.202008067 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Marchesi, Andrea
Parmeggiani, Fabio
Louçano, João
Mattey, Ashley P.
Huang, Kun
Gupta, Tanistha
Salwiczek, Mario
Flitsch, Sabine L.
Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly
title Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly
title_full Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly
title_fullStr Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly
title_full_unstemmed Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly
title_short Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly
title_sort enzymatic building‐block synthesis for solid‐phase automated glycan assembly
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756758/
https://www.ncbi.nlm.nih.gov/pubmed/32857448
http://dx.doi.org/10.1002/anie.202008067
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