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 language | English (US) |
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Pages (from-to) | 1167-1171 |
Number of pages | 5 |
Journal | The Journal of Antibiotics |
Volume | 33 |
Issue number | 10 |
DOIs | |
State | Published - 1980 |
Externally published | Yes |
ASJC Scopus subject areas
- Pharmacology
- Drug Discovery