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Type: Journal article
Title: Design and synthesis of a conformationally restricted trans peptide isostere based on the bioactive conformations of saquinavir and nelfinavir
Author: Edmonds, M.
Abell, A.
Citation: Journal of Organic Chemistry, 2001; 66(11):3747-3752
Publisher: Amer Chemical Soc
Issue Date: 2001
ISSN: 0022-3263
Statement of
Michael K. Edmonds and Andrew D. Abell
Abstract: The design and synthesis of a new peptide isostere which contains a trans alkene core is described. The key step involves a Wadsworth-Emmons reaction between chiral aldehyde (2S)-9a and chiral phosphonate 7 under base-sensitive conditions to give a chiral enone (2R)-24a which was reduced to afford the desired trans alkene isosteres (2R,5R)-6a and (2R,5S)-6b (Scheme 6). A potential application of this isostere in the synthesis of HIV protease inhibitors is also discussed.
Keywords: Nelfinavir; Saquinavir; HIV Protease Inhibitors; Anti-HIV Agents; Indicators and Reagents; Magnetic Resonance Spectroscopy; Spectrometry, Mass, Electrospray Ionization; Molecular Conformation
Description: Copyright © 2001 American Chemical Society
RMID: 0020064490
DOI: 10.1021/jo0016834
Appears in Collections:Chemistry publications

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