COMPLESTATIN TO CHLOROPEPTIN-I VIA A QUANTITATIVE ACID-CATALYZED REARRANGEMENT - ABSOLUTE STEREOCHEMICAL DETERMINATION OF COMPLESTATIN

Authors
JAYASURIYA H SALITURO GM SMITH SK HECK JV GOULD SJ SINGH SB HOMNICK CF HOLLOWAY MK PITZENBERGER SM PATANE MA
Citation
H. Jayasuriya et al., COMPLESTATIN TO CHLOROPEPTIN-I VIA A QUANTITATIVE ACID-CATALYZED REARRANGEMENT - ABSOLUTE STEREOCHEMICAL DETERMINATION OF COMPLESTATIN, Tetrahedron letters, 39(16), 1998, pp. 2247-2248
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
16
Year of publication
1998
Pages
2247 - 2248
Database
ISI
SICI code
0040-4039(1998)39:16<2247:CTCVAQ>2.0.ZU;2-J
Abstract
Complestatin and isomeric chloropeptin I are bicycle hexapeptides isol ated from a Streptomyces sp. Both of these compounds are inhibitors of gp120-CD4 HIV fusion activity. In this paper, we describe an efficien t acid catalyzed conversion of complestatin to chloropeptin I, provide a plausible mechanism for this transformation, and unambiguously assi gn the stereochemistry of complestatin. (C) 1998 Elsevier Science Ltd. All rights reserved.