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  • Title: Unequivocal synthesis of (Z)-alkene and (E)-fluoroalkene dipeptide isosteres to probe structural requirements of the peptide transporter PEPT1.
    Author: Niida A, Tomita K, Mizumoto M, Tanigaki H, Terada T, Oishi S, Otaka A, Inui K, Fujii N.
    Journal: Org Lett; 2006 Feb 16; 8(4):613-6. PubMed ID: 16468724.
    Abstract:
    [reaction: see text] 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 gamma-acetoxy- or gamma,gamma-difluoro-alpha,beta-unsaturated-delta-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.
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