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 |
| State | Published - 1990 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis of pyrimidoblamic acid and epipyrimidoblamic acid. / Aoyagi, Yoshiaki; Chorghade, Mukund S.; Padmapriya, Abeysinghe A.; Suguna, Hosbett; Hecht, Sidney.
In: Journal of Organic Chemistry, Vol. 55, No. 26, 1990, p. 6291-6298.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of pyrimidoblamic acid and epipyrimidoblamic acid
AU - Aoyagi, Yoshiaki
AU - Chorghade, Mukund S.
AU - Padmapriya, Abeysinghe A.
AU - Suguna, Hosbett
AU - Hecht, Sidney
PY - 1990
Y1 - 1990
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=0000658283&partnerID=8YFLogxK
M3 - Article
VL - 55
SP - 6291
EP - 6298
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 26
ER -