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Paper | Special issue | Vol 101, No. 1, 2020, pp.165-176
Published online, 20th June, 2019
DOI: 10.3987/COM-19-S(F)6
Synthesis of Optically Active (R)- and (S)-β-Arginine from Pyroglutamic Acid

Yoko Yasuno, Akira Sawai, Ai Sekihara, and Tetsuro Shinada*

*Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan

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.