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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Published inBeilstein journal of organic chemistry Vol. 18; no. 1; pp. 1133 - 1139
Main Authors Rahman, Md Azadur, Kuroda, Kana, Endo, Hirofumi, Sasaki, Norihiko, Hamada, Tomoaki, Sakai, Hiraku, Nokami, Toshiki
Format Journal Article
LanguageEnglish
Published Frankfurt am Main Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 30.08.2022
Beilstein-Institut
Subjects
By products
Chemistry
Chitin
electrochemical glycosylation
Electrolysis
Electrolytes
Full Research Paper
glucosamine
Monomers
oligosaccharide
Oligosaccharides
Oxidation
oxidation potential
polyglycosylation
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Summary: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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ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.18.117