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Antibacterial and antifungal nucleosides

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posted on 2016-06-07, 00:00 authored by Julia M. Dolence, Manuka Ghosh, Marvin J MillerMarvin J Miller
5'-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 B2

Other Application

08/745,732

Inventor

Marvin J. Miller Julia M. Dolence Manuka Ghosh

Inventor from Local Institution

Marvin J. Miller

Assignee

University of Notre Dame Du Lac

Date Modified

2016-06-07

Language

  • English

Claims

6

Publisher

United States Patent and Trademark Office

Cooperative Patent Classification Codes

C07H 19/06 (20130101)

Contributor

Marvin J. Miller

International 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;

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