An efficient synthesis of hydroxyethylene dipeptide isosteres: the core unit of potent HIV-1 protease inhibitors
- 1 November 1991
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 56 (23), 6500-6503
- https://doi.org/10.1021/jo00023a009
Abstract
An efficient and stereocontrolled synthesis of hydroxyethylene dipeptide isosteres 1 from commercially available, optically pure D-mannose is described. This synthesis represents a practical and enantioselective entry to a range of other dipeptide isosteres, which are not limited to amino acid derived substituents.Keywords
This publication has 13 references indexed in Scilit:
- An inhibitor of the protease blocks maturation of human and simian immunodeficiency viruses and spread of infection.Proceedings of the National Academy of Sciences, 1990
- A Synthetic HIV-1 Protease Inhibitor with Antiviral Activity Arrests HIV-Like Particle MaturationScience, 1990
- Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.Proceedings of the National Academy of Sciences, 1989
- HTLV-III gag Protein Is Processed in Yeast Cells by the Virus pol -ProteaseScience, 1986
- Frequent Detection and Isolation of Cytopathic Retroviruses (HTLV-III) from Patients with AIDS and at Risk for AIDSScience, 1984
- Isolation of a T-Lymphotropic Retrovirus from a Patient at Risk for Acquired Immune Deficiency Syndrome (AIDS)Science, 1983
- Renin-angiotensin system: biochemistry and mechanisms of action.Physiological Reviews, 1977
- Mode of inhibition of acid proteases by pepstatin.Journal of Biological Chemistry, 1976
- Diphenylphosphoryl azide. New convenient reagent for a modified Curtius reaction and for peptide synthesisJournal of the American Chemical Society, 1972
- Transition State Analogues for Enzyme CatalysisNature, 1969