Synthesis of partially modified retro and retroinverso ψ[NHCH(CF3)]-peptides

被引:71
作者
Volonterio, A
Bravo, P
Zanda, M
机构
[1] Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy
[2] CNR, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy
关键词
D O I
10.1021/ol005876p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric conjugate additions of chiral alpha-amino esters to chiral 4-CF3 Michael-acceptors were exploited to prepare a small library of enantiomerically pure partially modified retropeptides having a psi[NHCH(CF3)] 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.
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收藏
页码:1827 / 1830
页数:4
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