液相電解自動合成によるオリゴグルコサミンの合成

• 矢野 君晟

• 佐々木 紀彦

• 伊藤 敏幸

• 野上 敏材

  鳥取大学工学部化学バイオ系学科

書誌事項

タイトル別名

• Synthesis of Oligosaccharides of Glucosamine by Automated Electrochemical Assembly
• エキソウ デンカイ ジドウ ゴウセイ ニ ヨル オリゴグルコサミン ノ ゴウセイ

抄録

The automated electrochemical assembly is one of our arrial points for development of electrochemical methods for oligosaccharide synthesis. The one-pot sequential process of activation of thioglycoside building block by electrochemical oxidation and coupling with thioglycoside building block can be carried out in automated manner, and muliple cycles of the process enables us to synthesis oligosaccharides with desired chain length. We have synthesized oligoglucosamines with β-1,6- and β-1,4-glycosidic linkages. Total synthesis of TMG-chitotriomycin and Myc-IV (C16 : 0, S), which are biologically active oligoglucosamines derivatives, has also achieved. Ionic liquid tags were introduced to glucosamine building blocks to facilitate separation of products; however, they worked not only separation tag but also electrolyte and stereo-controlling group in electrochemical glycosylation. We also found that electrochemical glycosylation was also useful to convert linear oligosaccharides of glucosamines into the corresponding cyclic oligosaccharides.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 79 (9), 839-848, 2021-09-01

  公益社団法人 有機合成化学協会

キーワード

• oligosaccharides
• glucosamine
• automated synthesis
• electrochemical glycosylation

詳細情報

• CRID: 1390570784698378368
• NII論文ID: 130008085927
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.79.839
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 031709610
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I031709610
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/79/9/79_839/_pdf
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可