Synthesis of optically active (R)- And (S)-β-arginine from pyroglutamic acid

Yoko Yasuno, Akira Sawai, Ai Sekihara, Tetsuro Shinada

Research output: Contribution to journalArticle

Abstract

– The first synthesis of optically active β-arginine was achieved starting from commercially available pyroglutamic acid. The new synthetic protocol is characterized by the use of nitrile as a carboxylic acid surrogate which could be transformed to the corresponding 2-acyl-1,3-bis(1,1-dimethylethyl)imidodi-carbonic acid ester (active amide) via Pt-catalyzed hydration under the mild conditions. The active amide was converted to β-arginine and Boc-β-Arg-Val-OMe in good yield.

Original languageEnglish
Pages (from-to)165-176
Number of pages12
JournalHeterocycles
Volume101
Issue number1
DOIs
Publication statusPublished - Jan 1 2020
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of optically active (R)- And (S)-β-arginine from pyroglutamic acid'. Together they form a unique fingerprint.

  • Cite this