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Total synthesis of actinomycin D(C 1 ) via a ring‐opening reaction of aziridine
Author(s) -
Okawa K.,
Nakajima K.,
Tanaka T.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170840
Subject(s) - aziridine , chemistry , ring (chemistry) , stereochemistry , nitro , peptide , medicinal chemistry , organic chemistry , biochemistry , alkyl
Actinomycin D(C 1 ) has been synthesized by a route involving the ester formation between two peptide fragments, (2 S ,3 S )‐1‐(2‐nitro‐3‐benzyloxy‐4‐methylbenzoyl)‐3‐methyl‐2‐aziridine‐carbonyl‐D‐valylproline t ‐butyl ester and N ‐benzyloxycarbonylsarcosyl‐ N ‐methylvaline, via a ring‐opening reaction of aziridine. Cyclization, followed by reduction and oxidation, gave actinomycin D(C 1 ). The synthetic actinomycin D(C 1 ) was indistinguishable from natural substance with respect to physical properties and biological activity.