Synthesis of Protected Precursors of Chitin Oligosaccharides by Electrochemical Polyglycosylation of Thioglycosides

  1. Md Azadur Rahman,
  2. Kana Kuroda,
  3. Hirofumi Endo,
  4. Norihiko Sasaki,
  5. Tomoaki Hamada,
  6. Hiraku Sakai and
  7. Toshiki NokamiORCID Logo

Submitting author affiliation: Tottori University, Tottori city, Japan

Beilstein Arch. 2022, 202258. https://doi.org/10.3762/bxiv.2022.58.v1

Published 04 Jul 2022

  • Preprint

Abstract

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides as a monomer is described. Oligosaccharides up to hexasaccharide were synthesized under the optimized reaction conditions. The modified method by repeating electrolysis with additional monomers enabled synthesis of oligosaccharides up to octasaccharide. Mechanism of electrochemical polyglycosylation was also discussed based on the oxidation potentials of the monomer and oligosaccharides.

Keywords: electrochemical glycosylation; glucosamine; oligosaccharide; oxidation potential; polyglycosylation

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Rahman, M. A.; Kuroda, K.; Endo, H.; Sasaki, N.; Hamada, T.; Sakai, H.; Nokami, T. Beilstein Arch. 2022, 202258. doi:10.3762/bxiv.2022.58.v1

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© 2022 Rahman et al.; licensee Beilstein-Institut.
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