New Synthetic Methods for Benzyloxycarbonyl-l-arginine-p-nitroanilide, Benzoyl-l-arginine-p-nitroanilide, and Acetyl-l-arginine-p-nitroanilide
- 1 April 1978
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 51 (4) , 1255-1256
- https://doi.org/10.1246/bcsj.51.1255
Abstract
The optically active substrates for two peptidases, benzoyl-l-arginine-p-nitroanilide hydrochloride (l-BAPA·HCl) and acetyl-l-arginine-p-nitroanilide (l-AAPA·HCl), were readily prepared through the synthesis of benzyloxycarbonyl-l-arginine-p-nitroanilide hydrochloride (l-ZAPA·HCl). Benzyloxycarbonyl-l-arginine and p-nitroaniline were directly coupled without any racemization. The product, l-ZAPA·HCl, was quantitatively debenzyloxycarbonylated with hydrogen chloride in glacial acetic acid at 50 °C to l-arginine-p-nitroanilide dihydrochloride(l-APA·2HCl) which gave, on benzoylation or acetylation, l-BAPA·HCl or l-AAPA·HCl respectively.This publication has 5 references indexed in Scilit:
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