Unequivocal Synthesis of (Z)-Alkene and (E)-Fluoroalkene Dipeptide Isosteres To Probe Structural Requirements of the Peptide Transporter PEPT1

Described is a novel synthetic route for dipeptide isosteres containing (Z)-alkene and (E)-fluoroalkene units as cis-amide bond equivalents via organocopper-mediated reduction of γ-acetoxy- or γ,γ-difluoro-α,β-unsaturated-δ-lactams. The synthesized isosteres were evaluated in terms of their affiniti...

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Bibliographic Details
Published in:Organic letters 2006-02, Vol.8 (4), p.613-616
Main Authors: Niida, Ayumu, Tomita, Kenji, Mizumoto, Makiko, Tanigaki, Hiroaki, Terada, Tomohiro, Oishi, Shinya, Otaka, Akira, Inui, Ken-ichi, Fujii, Nobutaka
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Dipeptides - chemical synthesis
Dipeptides - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Molecular Structure
Peptide Transporter 1
Stereoisomerism
Symporters - chemistry
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Summary:Described is a novel synthetic route for dipeptide isosteres containing (Z)-alkene and (E)-fluoroalkene units as cis-amide bond equivalents via organocopper-mediated reduction of γ-acetoxy- or γ,γ-difluoro-α,β-unsaturated-δ-lactams. The synthesized isosteres were evaluated in terms of their affinities for the peptide transporter PEPT1. trans-Amide isosteres tended to possess higher affinities for PEPT1 as compared to the corresponding cis-amide bond equivalents.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052781k