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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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.18.117 |
| _version_ | 1818021487350644736 |
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| author | Md Azadur Rahman Kana Kuroda Hirofumi Endo Norihiko Sasaki Tomoaki Hamada Hiraku Sakai Toshiki Nokami |
| author_facet | Md Azadur Rahman Kana Kuroda Hirofumi Endo Norihiko Sasaki Tomoaki Hamada Hiraku Sakai Toshiki Nokami |
| author_sort | Md Azadur Rahman |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-14T08:18:41Z |
| format | Article |
| id | doaj.art-bd4ae0d60148479f9cd6b7709848052d |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-14T08:18:41Z |
| publishDate | 2022-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-bd4ae0d60148479f9cd6b7709848052d2022-12-22T02:04:18ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-08-011811133113910.3762/bjoc.18.1171860-5397-18-117Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosidesMd Azadur Rahman0Kana Kuroda1Hirofumi Endo2Norihiko Sasaki3Tomoaki Hamada4Hiraku Sakai5Toshiki Nokami6Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan Koganei Corporation, 3-11-28 Midorimachi, Koganei City, 184-8533 Tokyo, JapanKoganei Corporation, 3-11-28 Midorimachi, Koganei City, 184-8533 Tokyo, JapanDepartment of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan 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.https://doi.org/10.3762/bjoc.18.117electrochemical glycosylationglucosamineoligosaccharideoxidation potentialpolyglycosylation |
| spellingShingle | Md Azadur Rahman Kana Kuroda Hirofumi Endo Norihiko Sasaki Tomoaki Hamada Hiraku Sakai Toshiki Nokami Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides Beilstein Journal of Organic Chemistry electrochemical glycosylation glucosamine oligosaccharide oxidation potential polyglycosylation |
| title | Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides |
| title_full | Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides |
| title_fullStr | Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides |
| title_full_unstemmed | Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides |
| title_short | Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides |
| title_sort | synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides |
| topic | electrochemical glycosylation glucosamine oligosaccharide oxidation potential polyglycosylation |
| url | https://doi.org/10.3762/bjoc.18.117 |
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