Total synthesis of actinomycin D(C 1 )  via  a ring‐opening reaction of aziridine | Zendy

Okawa K. | Zendy; Nakajima K. | Zendy; Tanaka T. | Zendy

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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.

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