Synthesis of partially modified retro and retroinverso psi[NHCH(CF(3))]-peptides.
Synthesis of partially modified retro and retroinverso psi[NHCH(CF(3))]-peptides.
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部分修饰的反式和反式psi[NHCH(CF(3))]-肽的合成。
作者：
A. Volonterio;P. Bravo;M. Zanda
[反应：手性α-氨基酯与手性4-CF（3）迈克尔受体的不对称共轭加成被用于制备对映体纯的部分修饰的逆转录肽的小文库，所述逆转录肽具有psi[NHCH（CF（3））]单元作为经典psi（NHCO）逆转录肽单元的可能模拟物。产率几乎是定量的，并且主要由氮亲核试剂控制的立体选择性随着α-氨基酯侧链R（1）的空间体积的增加而逐渐升高。
[reaction: see text] Asymmetric conjugate additions of chiral alpha-amino esters to chiral 4-CF(3) Michael-acceptors were exploited to prepare a small library of enantiomerically pure partially modified retropeptides having a psi[NHCH(CF(3))] unit as a possible mimic of the classical psi(NHCO) retropeptide unit. Yields were nearly quantitative, and the stereoselectivity, which is controlled mainly by the nitrogen nucleophile, was progressively higher with increasing the steric bulk of the alpha-amino ester side-chain R(1).