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

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概要

• 論文の詳細を見る

• 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.

• 社団法人 日本農芸化学会の論文
• 2006-10-23

著者

• KOJIMA Naoya

  Department of Applied Biochemistry, Tokai University

• HOJO Hironobu

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• NAKAHARA Yuko

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• NAKAHARA Yoshiaki

  Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University

• KURODA Yasuhiro

  Department of Emergency and Critical Care Medicine, Kagawa University Hospital

• Nakamura Yu

  Nissei Hospital

• Kojima Naoya

  Tokai Univ. Kanagawa

• Kojima Naoya

  Department Of Applied Biochemistry Institute Of Glycotechnology Tokai University

• TANAKA Eriko

  Department of Pediatric Nephrology, Kidney Center, Tokyo Women's Medical University, School of Medic

• Tanaka Eriko

  Department Of Cardiovascular Medicine Kyushu University Graduate School Of Medical Sciences

• Nakahara Yoshiaki

  Department Of Applied Biochemistry Faculty Of Engineering Tokai University

• Nakahara Y

  Tokai Univ. Kanagawa Jpn

• Takano Yutaka

  Department Of Applied Biochemistry Institute Of Glycotechnology Tokai University

• Nakahara Y

  Department Of Applied Biochemistry Institute Of Glycoscience Tokai University

• Hojo H

  Department Of Applied Biochemistry Institute Of Glycoscience Tokai University

• Hojo Hironobu

  Department Of Applied Biochemistry Faculty Of Engineering Tokai University

• Kuroda Yasuhiro

  Department Of Emergency And Critical Care Medicine Kagawa University Hospital

• Tanaka Eriko

  Department Of Applied Biochemistry Institute Of Glycotechnology Tokai University

• Kuroda Yasuhiro

  Department Of Applied Biochemistry Institute Of Glycotechnology Tokai University

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