269399-35-1Relevant academic research and scientific papers
Epoxidation of peptidyl olefin isosteres. Stereochemical induction effect of chiral centers at four adjacent C(α) positions
Perlman, Nurit,Livneh, Mordechai,Albeck, Amnon
, p. 1505 - 1516 (2007/10/03)
Four tripeptidyl olefin isosteres were prepared, each of which contains a single chiral center derived from the bulky amino acid phenylalanine at positions corresponding to the P2-P'2 positions of a protease substrate. The effect of these chiral centers on the stereochemical outcome of mCPBA epoxidation of the olefin functionality was studied. A chiral center at P2 or P'2 position has no significant effect, and the P'1 position exerts a small stereoselectivity. A chiral center at the P1 position, on the other hand, has a profound chiral induction effect on the epoxidation reaction. (C) 2000 Elsevier Science Ltd.
