Synthesis of Partially Modified Retro and Retroinverso ψ[NHCH(CF3)]-Peptides
- 27 May 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (13) , 1827-1830
- https://doi.org/10.1021/ol005876p
Abstract
Asymmetric conjugate additions of chiral α-amino esters to chiral 4-CF3 Michael-acceptors were exploited to prepare a small library of enantiomerically pure partially modified retropeptides having a ψ[NHCH(CF3)] unit as a possible mimic of the classical ψ(NHCO) retropeptide unit. Yields were nearly quantitative, and the stereoselectivity, which is controlled mainly by the nitrogen nucleophile, was progressively higher with increasing the steric bulk of the α-amino ester side-chain R1.Keywords
This publication has 9 references indexed in Scilit:
- Protease Inhibitors: Current Status and Future ProspectsJournal of Medicinal Chemistry, 2000
- Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational BehaviorChemical Reviews, 1998
- Pseudopeptide CCK-4 analogues incorporating the Ψ[CH(CN)NH] peptide bond surrogateBioorganic & Medicinal Chemistry Letters, 1997
- Novel Binding Mode of Hydroxamate Inhibitors to Human Carbonic Anhydrase IIJournal of the American Chemical Society, 1997
- A highly diastereoselective synthesis of trans-3,4-(difluoromethano)glutamic acidTetrahedron, 1996
- Peptidomimetics—Tailored Enzyme InhibitorsAngewandte Chemie International Edition in English, 1994
- Concepts and progress in the development of peptide mimeticsJournal of Medicinal Chemistry, 1993
- On the concept of linear modified retro-peptide structuresAccounts of Chemical Research, 1979
- A general approach to retro-isomeric linear peptide synthesisJournal of the American Chemical Society, 1977