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 language | English (US) |
|---|---|
| Pages (from-to) | 6291-6298 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 55 |
| Issue number | 26 |
| DOIs | |
| State | Published - Jan 1 1990 |
| Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry
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Cite this
Aoyagi, Y., Chorghade, M. S., Padmapriya, A. A., Suguna, H., & Hecht, S. M. (1990). Synthesis of Pyrimidoblamic Acid and Epipyrimidoblamic Acid. Journal of Organic Chemistry, 55(26), 6291-6298. https://doi.org/10.1021/jo00313a016