Cargando…

Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides

Electrochemical glycosylation of a linear oligosaccharide with a protecting‐group‐free primary hydroxyl group afforded cyclic oligo‐saccharides, up to hexasaccharides, in high yields. Precursors of the cyclic oligosaccharides were prepared by automated electro‐chemical assembly‐a method for the auto...

Descripción completa

Detalles Bibliográficos
Autores principales: Manmode, Sujit, Tanabe, Shichidai, Yamamoto, Takashi, Sasaki, Norihiko, Nokami, Toshiki, Itoh, Toshiyuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6607414/
https://www.ncbi.nlm.nih.gov/pubmed/31309034
http://dx.doi.org/10.1002/open.201900185
_version_ 1783432092447670272
author Manmode, Sujit
Tanabe, Shichidai
Yamamoto, Takashi
Sasaki, Norihiko
Nokami, Toshiki
Itoh, Toshiyuki
author_facet Manmode, Sujit
Tanabe, Shichidai
Yamamoto, Takashi
Sasaki, Norihiko
Nokami, Toshiki
Itoh, Toshiyuki
author_sort Manmode, Sujit
collection PubMed
description Electrochemical glycosylation of a linear oligosaccharide with a protecting‐group‐free primary hydroxyl group afforded cyclic oligo‐saccharides, up to hexasaccharides, in high yields. Precursors of the cyclic oligosaccharides were prepared by automated electro‐chemical assembly‐a method for the automated electrochemical solution‐phase synthesis of oligosaccharides. We demonstrated that electrochemical glycosylation is useful not only for intermolecular glycosylation but also for intramolecular glycosylation to synthesize cyclic oligosaccharides.
format Online
Article
Text
id pubmed-6607414
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-66074142019-07-15 Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides Manmode, Sujit Tanabe, Shichidai Yamamoto, Takashi Sasaki, Norihiko Nokami, Toshiki Itoh, Toshiyuki ChemistryOpen Communications Electrochemical glycosylation of a linear oligosaccharide with a protecting‐group‐free primary hydroxyl group afforded cyclic oligo‐saccharides, up to hexasaccharides, in high yields. Precursors of the cyclic oligosaccharides were prepared by automated electro‐chemical assembly‐a method for the automated electrochemical solution‐phase synthesis of oligosaccharides. We demonstrated that electrochemical glycosylation is useful not only for intermolecular glycosylation but also for intramolecular glycosylation to synthesize cyclic oligosaccharides. John Wiley and Sons Inc. 2019-07-03 /pmc/articles/PMC6607414/ /pubmed/31309034 http://dx.doi.org/10.1002/open.201900185 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Manmode, Sujit
Tanabe, Shichidai
Yamamoto, Takashi
Sasaki, Norihiko
Nokami, Toshiki
Itoh, Toshiyuki
Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides
title Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides
title_full Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides
title_fullStr Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides
title_full_unstemmed Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides
title_short Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides
title_sort electrochemical glycosylation as an enabling tool for the stereoselective synthesis of cyclic oligosaccharides
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6607414/
https://www.ncbi.nlm.nih.gov/pubmed/31309034
http://dx.doi.org/10.1002/open.201900185
work_keys_str_mv AT manmodesujit electrochemicalglycosylationasanenablingtoolforthestereoselectivesynthesisofcyclicoligosaccharides
AT tanabeshichidai electrochemicalglycosylationasanenablingtoolforthestereoselectivesynthesisofcyclicoligosaccharides
AT yamamototakashi electrochemicalglycosylationasanenablingtoolforthestereoselectivesynthesisofcyclicoligosaccharides
AT sasakinorihiko electrochemicalglycosylationasanenablingtoolforthestereoselectivesynthesisofcyclicoligosaccharides
AT nokamitoshiki electrochemicalglycosylationasanenablingtoolforthestereoselectivesynthesisofcyclicoligosaccharides
AT itohtoshiyuki electrochemicalglycosylationasanenablingtoolforthestereoselectivesynthesisofcyclicoligosaccharides