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 in | Beilstein journal of organic chemistry Vol. 18; no. 1; pp. 1133 - 1139 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
Frankfurt am Main
Beilstein-Institut zur Föerderung der Chemischen Wissenschaften
30.08.2022
Beilstein-Institut |
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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. |
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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 – name: 3 Koganei Corporation, 3-11-28 Midorimachi, Koganei City, 184-8533 Tokyo, Japan |
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Cites_doi | 10.3762/bjoc.13.93 10.3762/bjoc.17.129 10.1002/marc.1996.030170601 10.1021/ol402034g 10.1021/ja072440x 10.1021/acs.jafc.0c05316 10.1021/acs.orglett.5b00406 10.1080/07328308908048012 10.1039/d2cc02287g 10.1016/j.tet.2013.11.064 |
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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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