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
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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.
AbstractList 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.
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.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.
Author Hamada, Tomoaki
Rahman, Md Azadur
Endo, Hirofumi
Sakai, Hiraku
Sasaki, Norihiko
Nokami, Toshiki
Kuroda, Kana
AuthorAffiliation 2 Center for Research on Green Sustainable Chemistry, Faculty of Engineering, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan https://ror.org/024yc3q36 https://www.isni.org/isni/0000000106635064
3 Koganei Corporation, 3-11-28 Midorimachi, Koganei City, 184-8533 Tokyo, Japan
1 Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan https://ror.org/024yc3q36 https://www.isni.org/isni/0000000106635064
AuthorAffiliation_xml – name: 2 Center for Research on Green Sustainable Chemistry, Faculty of Engineering, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan https://ror.org/024yc3q36 https://www.isni.org/isni/0000000106635064
– name: 1 Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan https://ror.org/024yc3q36 https://www.isni.org/isni/0000000106635064
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CitedBy_id crossref_primary_10_1016_j_coelec_2024_101457
crossref_primary_10_1039_D4CC04877F
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10.3762/bjoc.17.129
10.1002/marc.1996.030170601
10.1021/ol402034g
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10.1021/acs.orglett.5b00406
10.1080/07328308908048012
10.1039/d2cc02287g
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StartPage 1133
SubjectTerms By products
Chemistry
Chitin
electrochemical glycosylation
Electrolysis
Electrolytes
Full Research Paper
glucosamine
Monomers
oligosaccharide
Oligosaccharides
Oxidation
oxidation potential
polyglycosylation
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Title Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides
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