Literature DB >> 30393394

An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors.

Arun K Ghosh1, Sean P McKee1, Wayne J Thompson1.   

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.

Entities:  

Year:  1991        PMID: 30393394      PMCID: PMC6214462          DOI: 10.1021/jo00023a009

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  14 in total

Review 1.  Renin-angiotensin system: biochemistry and mechanisms of action.

Authors:  M J Peach
Journal:  Physiol Rev       Date:  1977-04       Impact factor: 37.312

2.  HTLV-III gag protein is processed in yeast cells by the virus pol-protease.

Authors:  R A Kramer; M D Schaber; A M Skalka; K Ganguly; F Wong-Staal; E P Reddy
Journal:  Science       Date:  1986-03-28       Impact factor: 47.728

3.  Diphenylphosphoryl azide. A new convenient reagent for a modified Curtus reaction and for the peptide synthesis.

Authors:  T Shioiri; K Ninomiya; S Yamada
Journal:  J Am Chem Soc       Date:  1972-08-23       Impact factor: 15.419

4.  Transition state analogues for enzyme catalysis.

Authors:  R Wolfenden
Journal:  Nature       Date:  1969-08-16       Impact factor: 49.962

5.  An inhibitor of the protease blocks maturation of human and simian immunodeficiency viruses and spread of infection.

Authors:  P Ashorn; T J McQuade; S Thaisrivongs; A G Tomasselli; W G Tarpley; B Moss
Journal:  Proc Natl Acad Sci U S A       Date:  1990-10       Impact factor: 11.205

Review 6.  Renin inhibitors.

Authors:  W J Greenlee
Journal:  Med Res Rev       Date:  1990 Apr-Jun       Impact factor: 12.944

7.  Mode of inhibition of acid proteases by pepstatin.

Authors:  J Marciniszyn; J A Hartsuck; J Tang
Journal:  J Biol Chem       Date:  1976-11-25       Impact factor: 5.157

8.  Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS).

Authors:  F Barré-Sinoussi; J C Chermann; F Rey; M T Nugeyre; S Chamaret; J Gruest; C Dauguet; C Axler-Blin; F Vézinet-Brun; C Rouzioux; W Rozenbaum; L Montagnier
Journal:  Science       Date:  1983-05-20       Impact factor: 47.728

9.  Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.

Authors:  G B Dreyer; B W Metcalf; T A Tomaszek; T J Carr; A C Chandler; L Hyland; S A Fakhoury; V W Magaard; M L Moore; J E Strickler
Journal:  Proc Natl Acad Sci U S A       Date:  1989-12       Impact factor: 11.205

10.  Frequent detection and isolation of cytopathic retroviruses (HTLV-III) from patients with AIDS and at risk for AIDS.

Authors:  R C Gallo; S Z Salahuddin; M Popovic; G M Shearer; M Kaplan; B F Haynes; T J Palker; R Redfield; J Oleske; B Safai
Journal:  Science       Date:  1984-05-04       Impact factor: 47.728

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