Synthesis of Pyrimidoblamic Acid and Epipyrimidoblamic Acid

Yoshiaki Aoyagi, Mukund S. Chorghade, Abeysinghe A. Padmapriya, Hosbett Suguna, Sidney M. Hecht

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

The N-protected pyrimidine moieties of bleomycin (pyrimidoblamic acid, 1) and epibleomycin are reported. In addition to a complete description of a synthetic route outlined earlier (Arai, H.; Hagmann, W. K.; Suguna, H.; Hecht, S. M. J. Am. Chem. Soc 1980, 102, 6631), a new route is also presented that provides access to multigram quantities of pyrimidoblamic acid. Because bleomycin and epibleomycin, which differ only in the orientation of the propionamide substituent, differ significantly in their Cu(II) chelation and DNA cleavage properties, we also prepared an analogue of pyrimidoblamic acid lacking the propionamide moiety.

Original languageEnglish (US)
Pages (from-to)6291-6298
Number of pages8
JournalJournal of Organic Chemistry
Volume55
Issue number26
DOIs
StatePublished - Jan 1 1990
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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