N(Ï)-2-Naphthylmethoxymethyl-Protected Histidines: Scalable, Racemization-Free Building Blocks for Peptide Synthesis

Kohei Torikai, Ryota Yanagimoto, Louis A. Watanabe

研究成果: Contribution to journalArticle査読

3 被引用数 (Scopus)

抄録

Histidine (His) racemizes with relative ease during peptide synthesis. One strategy to suppress this racemization is to protect the nitrogen atom of the imidazole moiety in His with a suitable protecting group. Among the numerous protecting groups that have already been tested, the p-methoxybenzyloxymethyl (PMBOM) group on the Ï-nitrogen atom effectively suppresses the racemization. However, a large-scale synthesis of N(Ï)-PMBOM-protected derivatives has hitherto been hampered by the requirement of a freshly prepared unstable reagent. Herein we report the synthesis of N(Ï)-2-naphthylmethoxymethyl (NAPOM)-protected His derivatives, which can be prepared on a gram scale and do not suffer from the aforementioned instability problems. Furthermore, these NAPOM-protected His derivatives suppress the racemization in Boc- A nd Fmoc-based peptide synthesis.

本文言語英語
ページ(範囲)448-453
ページ数6
ジャーナルOrganic Process Research and Development
24
3
DOI
出版ステータス出版済み - 3 20 2020

All Science Journal Classification (ASJC) codes

  • 物理化学および理論化学
  • 有機化学

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