Studies Relating to Aziridine Antitumor Antibiotics. Part II. 13C and 1H Nuclear Magnetic Resonance Spectra of Mitomycin C and Structurally Related Streptonigrin

Abstract

Double irradiation experiments in the 100 MHz n.m.r. spectrum of mitomycin C allowed determination of vicinal coupling constants which provide information on the conformation of the antibiotic in solution. The natural abundance 13C spectrum and comparison with selected model compounds allowed assignment of the carbon resonances of mitomycin C. The 13C chemical shifts of the quinone ring carbons in mitomycin C have a bearing on the proposed stabilization in vivo. Similar studies on the antitumor antibiotic streptonigrin bearing the common aminoquinone moiety gave indications of conjugative interactions similar to those established for mitomycin C.