Unequivocal synthesis of (Z)-alkene and (E)-fluoroalkene dipeptide isosteres to probe structural requirements of the peptide transporter PEPT1
Unequivocal synthesis of (Z)-alkene and (E)-fluoroalkene dipeptide isosteres to probe structural requirements of the peptide transporter PEPT1
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DOI：
10.1021/ol052781k
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发表时间：
2006-02-16
期刊：
影响因子：
5.2
通讯作者：
Fujii, N
中科院分区：
文献类型：
--
作者：
Niida, A;Tomita, K;Fujii, N
描述了一种新的合成途径，通过有机铜介导的γ -乙酰氧基或γ -二氟- α - β -不饱和δ内酰胺的还原，合成含有(Z)-烯烃和(E)-氟烯烃单元的顺酰胺键当量的二肽同位异构体。合成的同分异构体根据其对肽转运体PEPT1的亲和力进行了评估。与相应的顺酰胺键等价物相比，陷阱酰胺同异构体倾向于对PEPT1具有更高的亲和力。
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. traps-Amide isosteres tended to possess higher affinities for PEPT1 as compared to the corresponding cis-amide bond equivalents.