Studies on Peptides. CLV. : Evaluation of Trimethylsilyl Bromide as a Hard-Acid Deprotecting Reagent in Peptide Synthesis(Organic,Chemical)

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概要

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• Trimethylsilyl bromide (TMSBr) in trifluoroacetic acid (TFA) was found to have the ability to cleave benzyl-type protecting groups, i.e., benzyloxycarbonyl (Z), benzyl (O-Bzl) and p-methoxy-benzyl (S-MBzl). The reaction was best accelerated by addition of thioanisole, compared with other soft nucleophiles so far examined. The rate of the cleavage reaction with TMSBr/TFA was judged to be somewhat slower than that with trimethylsilyl trifluoromethanesulfonate/TFA. However, TMSBr/TFA reduced Met(O) efficiently and gave almost no side reaction of Asp (succinimide formation). This deprotecting procedure was applied to the synthesis of human gastrin-releasing peptide.

• 公益社団法人日本薬学会の論文
• 1987-09-25

著者

• FUJII Nobutaka

  Faculty of Pharmaceutical Sciences, Kyoto University

• Otaka Akira

  Faculty Of Pharmaceutical Sciences Kyoto University

• Fujii Nobutaka

  Faculty Of Pharmaceutical Science Kyoto University

• SUGIYAMA NAOKI

  Faculty of Pharmaceutical Sciences, Kyoto University

• YAJIMA HARUAKI

  Faculty of Pharmaceutical Sciences, Kyoto University

• Yajima H

  Kyoto Univ. Kyoto Jpn

• Yajima Haruaki

  Faculty Of Pharmaceutical Sciences Kyoto University

• Sugiyama N

  Green Cross Corp. Osaka Jpn

• Otaka A

  Kyoto Univ. Kyoto Jpn

• Sugiyama Naoki

  Faculty Of Pharmaceutical Sciences Kyoto University

• HATANO MIKA

  Faculty of Pharmaceutical Sciences, Kyoto University

• Hatano M

  Kyoto Univ. Kyoto Jpn

• Okamachi A

  Fuji-gotemba Research Laboratories Chugai Pharmaceutical Co.ltd.

• YAJIMA HARUAKI

  Faculty of Pharmaceutical Science, Kyoto University

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