Chemoenzymatic Synthesis of a MUC1 Glycopeptide Carrying Non-Natural Sialyl TF-β O-Glycan

• TANAKA Eriko

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• NAKAHARA Yuko

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• KURODA Yasuhiro

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• TAKANO Yutaka

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• KOJIMA Naoya

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• HOJO Hironobu

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• NAKAHARA Yoshiaki

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

書誌事項

タイトル別名

• Chemoenzymatic Synthesis of a MUC1 Glycopeptide Carrying Non-Natural Sialyl TF-.BETA. O-Glycan
• Chemoenzymatic Synthesis of a MUC1 Glycopeptide Carrying Non Natural Sialyl TF ベータ O Glycan
• Chemoenzymatic Synthesis of a MUC1 Glycopeptide Carrying Non-Natural Sialyl TF-β<i>O</i>-Glycan

抄録

A MUC1 type of glycopeptide was synthesized by the 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) protocol using benzyl and benzylidene-protected β-D-Gal-(1→3)-β-D-GalNAc-Ser/Thr (TF-β: a stereoisomer of the Thomsen-Friedenreich antigen). The synthetic glycopeptide was released from the resin with reagent K, and the resulting benzylated glycopeptide was deprotected under conditions of low-acidity trifluoromethanesulfonic acid (TfOH). The glycopeptide carrying duplicate non-natural O-glycans was dominant in the products, but was accompanied by a considerable amount of the glycopeptide missing one of the O-glycans. In contrast, the native α-glycoside was relatively stable under the acidic debenzylation conditions as shown by a parallel experiment with the glycopeptide involving α-D-GalNAc-Ser/Thr linkage. Enzymatic glycosylation with CMP-NeuAc was successful with both natural and non-natural O-glycans of the synthetic glycopeptide.

収録刊行物

• Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ

  Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ 70 (10), 2515-2522, 2006

  公益社団法人 日本農芸化学会

キーワード

• core 1 <I>O</I>-glycan
• glycopeptide
• solid-phase synthesis
• MUC1
• sialyltransferase

詳細情報

• CRID: 1390282681454070144
• NII論文ID: 10018526076
• NII書誌ID: AA10824164
• DOI: 10.1271/bbb.60244
• ISSN: 13476947
• ISSN: 09168451
• NDL書誌ID: 8524159
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8524159
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.60244
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
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