Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

The synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides as monomer is described. Oligosaccharides up to the hexasaccharide were synthesized under optimized reaction conditions. Further, a modified method enabled the synthesis of oligosa...

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Autores principales: Rahman, Md Azadur, Kuroda, Kana, Endo, Hirofumi, Sasaki, Norihiko, Hamada, Tomoaki, Sakai, Hiraku, Nokami, Toshiki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443410/
https://www.ncbi.nlm.nih.gov/pubmed/36105733
http://dx.doi.org/10.3762/bjoc.18.117
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author Rahman, Md Azadur
Kuroda, Kana
Endo, Hirofumi
Sasaki, Norihiko
Hamada, Tomoaki
Sakai, Hiraku
Nokami, Toshiki
author_facet Rahman, Md Azadur
Kuroda, Kana
Endo, Hirofumi
Sasaki, Norihiko
Hamada, Tomoaki
Sakai, Hiraku
Nokami, Toshiki
author_sort Rahman, Md Azadur
collection PubMed
description The synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides as monomer is described. Oligosaccharides up to the hexasaccharide were synthesized under optimized reaction conditions. Further, a modified method enabled the synthesis of oligosaccharides up to the octasaccharide by repeating electrolysis with additional monomers. The mechanism of the electrochemical polyglycosylation is also discussed, based on the oxidation potential of the monomer and oligosaccharides.
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spelling pubmed-94434102022-09-13 Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides Rahman, Md Azadur Kuroda, Kana Endo, Hirofumi Sasaki, Norihiko Hamada, Tomoaki Sakai, Hiraku Nokami, Toshiki Beilstein J Org Chem Full Research Paper The synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides as monomer is described. Oligosaccharides up to the hexasaccharide were synthesized under optimized reaction conditions. Further, a modified method enabled the synthesis of oligosaccharides up to the octasaccharide by repeating electrolysis with additional monomers. The mechanism of the electrochemical polyglycosylation is also discussed, based on the oxidation potential of the monomer and oligosaccharides. Beilstein-Institut 2022-08-30 /pmc/articles/PMC9443410/ /pubmed/36105733 http://dx.doi.org/10.3762/bjoc.18.117 Text en Copyright © 2022, Rahman et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Rahman, Md Azadur
Kuroda, Kana
Endo, Hirofumi
Sasaki, Norihiko
Hamada, Tomoaki
Sakai, Hiraku
Nokami, Toshiki
Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
title Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
title_full Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
title_fullStr Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
title_full_unstemmed Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
title_short Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
title_sort synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443410/
https://www.ncbi.nlm.nih.gov/pubmed/36105733
http://dx.doi.org/10.3762/bjoc.18.117
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