US5783689.pdf (1.13 MB)
Antibacterial and antifungal nucleosides
standard
posted on 2016-06-07, 00:00 authored by Julia M. Dolence, Manuka Ghosh, Marvin J MillerMarvin J Miller5'-O-Acyl-5-fluorouridines and 5'-O-acyl-5-sluorocytidines are prepared by the direct acylation of the 5'-hydroxyl group with amino acids under Mitsunobu conditions and the amino acyl derivatives are coupled with other amino acids or peptides to provide antibacterial and antifungal derivatives of the nucleosides. For example, 5-fluorouridine is acylated at the 5'-hydroxyl group with an amino protected L-valine and the acylation product is deprotected to provide 5'-O-(L-valinyl)-5-fluorouridine having activity against Gram-positive bacteria including resistant staphylococcus. Preferred peptide derivatives comprise the tripeptides of ornithine and lysine wherein the terminal amino group is substituted by both hydroxy and acetyl. The latter peptides inhibit the growth of C. albicans.
History
Patent Number
US 5783689 B2Other Application
08/745,732Inventor
Marvin J. Miller Julia M. Dolence Manuka GhoshInventor from Local Institution
Marvin J. MillerAssignee
University of Notre Dame Du LacDate Modified
2016-06-07Language
- English
Claims
6Publisher
United States Patent and Trademark OfficeCooperative Patent Classification Codes
C07H 19/06 (20130101)Contributor
Marvin J. MillerInternational Patent Classification Codes
C07H 19/06 (20060101); C07H 19/00 (20060101); C07H 019/067 ()US Patent Classification Codes
536/28.52; 530/350; 536/28.55;Usage metrics
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