Chemical conversion of anthramycin 11-methyl ether to didehydroanhydroanthramycin and its utilization in studies of the biosynthesis and mechanism of action of anthramycin

Ravindra K. Malhotra, John M. Ostrander, Laurence H. Hurley, A. G. McInnes, D. G. Smith, J. A. Walter, J. L.C. Wright

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Reaction of anthramycin 11-methyl ether (AME) with trifluoroacetic acid results in formation of (1,11a)-didehydroanhydroanthramycin (DAA). Anthramycin biosynthetically labelled from DL-[3'RS(3'-3H)]; DL-[3'S(3'-3H)] and DL-[3'S(3'-3H)]tyrosine each lose approximately 50% of their tritium during this conversion to DAA confirming the labelling pattern of 3'-tritiated species of tyrosine in AME. As expected negligible losses of tritium occurred from AME biosynthetically labelled from L-[2- or 6-3H] or L-[3- or 5-3H]tyrosine. DAA did not form a stable adduct with DNA in accord with the postulated mechanism of action of anthramycin.

Original languageEnglish (US)
Pages (from-to)38-44
Number of pages7
JournalJournal Of Natural Products
Volume44
Issue number1
DOIs
StatePublished - Jan 1981

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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