Biosynthesis of anthramycin. Determination of the labeling pattern by the use of radioactive and stable isotope techniques

Laurence Hurley, Milton Zmijewski, Ching Jer Chang

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The building blocks for anthramycin, an antitumor antibiotic produced by a strain of Streptomyces refuineus, have been shown to be L-tryptophan, probably via 3-hydroxyanthranilic acid, L-tyrosine which loses two of its aromatic carbons, and L-methionine which contributes two methyl groups. While one of the two methyl groups is transferred intact, the other loses all of its hydrogens and becomes the carbonyl of an amide group. A mechanism involving extradiol cleavage of Dopa is proposed on the basis of double labeling and stable isotope experiments. A general scheme for the biosynthetic origin of the C3-proline moieties of anthramycin, lincomycin A, and sibiromycin and the C2-proline moieties of tomaymycin and lincomycin B is proposed.

Original languageEnglish (US)
Pages (from-to)4372-4378
Number of pages7
JournalJournal of the American Chemical Society
Volume97
Issue number15
StatePublished - 1975
Externally publishedYes

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Anthramycin
Biosynthesis
Antibiotics
Amides
Proline
Radioisotopes
Isotopes
Labeling
3-Hydroxyanthranilic Acid
Lincomycin
Isotope Labeling
Hydrogen
Dihydroxyphenylalanine
Carbon
Acids
Streptomyces
Tryptophan
Methionine
Tyrosine
Experiments

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Biosynthesis of anthramycin. Determination of the labeling pattern by the use of radioactive and stable isotope techniques. / Hurley, Laurence; Zmijewski, Milton; Chang, Ching Jer.

In: Journal of the American Chemical Society, Vol. 97, No. 15, 1975, p. 4372-4378.

Research output: Contribution to journalArticle

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