Synthesis of partially modified retro and retroinverso psi[NHCH(CF(3))]-peptides.
[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).
Volonterio
A
A
Dipartimento di Chimica del Politecnico di Milano, via Mancinelli 7, I-20131 Milano, Italy. alessandro.volonterio@dept.chem.polimi.it
Bravo
P
P
Zanda
M
M
D001671:Biochemistry / Q000379:methods*; D018716:Molecular Mimicry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
D010455:Peptides