Proof for the biosynthetic conversion of L-[Indole-15N]Tryptophan to [10-15N]Anthramycin using (13C, 15N) labelling in conjunction with 13C-NMR and mass spectral analysis

J. M. Ostrander, L. H. Hurley, A. Gavin McInnes, D. G. Smith, Jeffrey L. Wright, John A. Walter

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 16N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[l-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-16N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 16N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.

Original languageEnglish (US)
Pages (from-to)1167-1171
Number of pages5
JournalThe Journal of Antibiotics
Volume33
Issue number10
DOIs
StatePublished - Jan 1 1980
Externally publishedYes

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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