Total synthesis of a pepstatin analog incorporating two trifluoromethyl hydroxymethylene isosteres (Tfm-GABOB) and evaluation of Tfm-GABOB containing peptides as inhibitors of HIV-1 protease and MMP-9

Cristina Pesenti, Alberto Arnone, Stefano Bellosta, Pierfrancesco Bravo, Monica Canavesi, Eleonora Corradi, Massimo Frigerio, Stefano V. Meille, Mara Monetti, Walter Panzeri, Fiorenza Viani, Romina Venturini, Matteo Zanda

Research output: Contribution to journalArticlepeer-review

Abstract

We describe the asymmetric total synthesis of a trifluoromethyl (Tfm) analogue of the aspartate protease inhibitor pepstatin incorporating two γ-Tfm-γ-amino-β-hydroxybutyric acid (γ-Tfm-GABOB) units instead of the natural statine units. The title compound as well as several Tfm-substituted precursors were tested as inhibitors of HIV-1 protease and Gelatinase B (MMP-9)

Original languageEnglish
Pages (from-to)6511-6522
Number of pages12
JournalTetrahedron
Volume57
Issue number30
DOIs
Publication statusPublished - Jul 23 2001

Keywords

  • Asymmetric synthesis
  • HIV
  • Metalloproteinase
  • Peptide isosteres
  • Trifluoromethyl group

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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