Unequivocal Synthesis of (Z)-Alkene and (E)-Fluoroalkene Dipeptide Isosteres To Probe Structural Requirements of the Peptide Transporter PEPT1
Organic Letters2006Vol. 8(4), pp. 613–616
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Ayumu Niida, Kenji Tomita, Makiko Mizumoto, Hiroaki Tanigaki, Tomohiro Terada, Shinya Oishi, Akira Otaka, Ken‐ichi Inui, Nobutaka Fujii
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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