Amino Acids and Peptides. L. Development of a Novel N^π-Protecting Group for Histidine, N^π-2-Adamantyloxymethylhistidine, and Its Application to peptide Synthesis

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概要

• 論文の詳細を見る

• N^α-tert-Butyloxycarbonyl-N^π-2-adamantyloxymethylhistidine, Boc-His(N^π-2-Adom)-OH, was prepared by the reaction of Boc-His (N^τ-Boc)-OMe with 2-adamantyloxymethyl chloride (2-Adom-Cl), followed by saponification. The 2-Adom group was stable to trifluoroacetic acid (TFA), 1 N NaOH and 20% piperidine/DMF and easily removed by 1 M trifluoromethanesulfonic acid-thioanisole/TFA and HF. This new protecting group suppressed recemization during peptide synthesis and exhibited high solubility in organic solvents. It was applied to the synthesis of thyrotropin-releasing hormone (TRH) using both solution and solid-phase methods. The N^π-2-Adom group can be used for peptide synthesis in combination with the tert-butyloxycarbonyl group as the N^d-protecting group in both solution and solid-phase methods.

• 公益社団法人日本薬学会の論文
• 1997-03-15

著者

• OKADA Yoshio

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• WANG Jidong

  Department of Synchrotron Radiation Science, The Graduate University for Advanced Studies

• Okada Yoshio

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• YOKOI Toshio

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• YOKOI Toshio

  The Graduate School of Food and Medicinal Sciences, Kobe Gakuin University

• MU Yu

  Faculty of Pharmaceutical Sciences, Osaka University

• Mu Y

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Mu Yu

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Wang J

  Shenyang Pharmaceutical Univ. Shenyang Chn

• Yokoi T

  Faculty Of Pharmaceutical Sciences And High-technology Research Center Kobe-gakuin University

• Yokoi T

  Kobe‐gakuin Univ. Hyogo Jpn

• Yamamoto T

  R&d Laboratories Nippon Organon K.k.

• YAMAMOTO Takeshi

  (Present address)New Drug Research Laboratory, Kanebo Ltd.,

• Wang Jidong

  Department Of Synchrotron Radiation Science The Graduate University For Advanced Studies

• Yokoi Toshio

  Faculty Of Pharmaceutical Sciences And High-technology Research Center Kobe-gakuin University

• Wang Jidong

  Department Of Molecular Biology Jilin University

• Wang J

  Department Of Synchrotron Radiation Science The Graduate University For Advanced Studies

• Yokoi T

  Fucunlty Of Pharmaceutical Sciences Kobe Gakuin University

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