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

Authors
Pesenti, C Arnone, A Bellosta, S Bravo, P Canavesi, M Corradi, E Frigerio, M Meille, SV Monetti, M Panzeri, W Viani, F Venturini, R Zanda, M
Citation
C. Pesenti et al., Total synthesis of a pepstatin analog incorporating two trifluoromethyl hydroxymethylene isosteres (Tfm-GABOB) and evaluation of Tfm-GABOB containingpeptides as inhibitors of HIV-1 protease and MMP-9, TETRAHEDRON, 57(30), 2001, pp. 6511-6522
Citations number
49
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
30
Year of publication
2001
Pages
6511 - 6522
Database
ISI
SICI code
0040-4020(20010723)57:30<6511:TSOAPA>2.0.ZU;2-Q
Abstract
We describe the asymmetric total synthesis of a trifluoromethyl (Tfm) analo gue of the aspartate protease inhibitor pepstatin incorporating two gamma - Tfm-gamma -amino-beta -hydroxybutyric acid (gamma -Tfm-GABOB) units instead of the natural statine units. The title compound as well as several Tfm-su bstituted precursors were tested as inhibitors of HIV-1 protease and Gelati nase B (MMP-9) (C) 2001 Elsevier Science Ltd. All rights reserved.