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

ABSTRACT: 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.

SUBMITTER: Rahman MA

PROVIDER: S-EPMC9443410 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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

Rahman Md Azadur MA Kuroda Kana K Endo Hirofumi H Sasaki Norihiko N Hamada Tomoaki T Sakai Hiraku H Nokami Toshiki T

Beilstein journal of organic chemistry 20220830

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 ...[more]

PMID: 36105733

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