269399-33-9Relevant academic research and scientific papers
Optically active N- and C-terminal building blocks for the synthesis of peptidyl olefin peptidomimetics
Mirilashvili, Sima,Chasid-Rubinstein, Naama,Albeck, Amnon
experimental part, p. 4671 - 4686 (2010/10/19)
Peptidyl olefin peptidomimetics serve as biologically active compounds or as intermediates for other peptidyl isosteres. The N-terminal side of the C=C bond could be easily prepared in an optically pure form from α-amino acids. Synthesis of C-terminal building blocks in an optically pure form is more challenging. We developed a chemoenzymatic stereoselective approach to such optically active C-terminal building blocks to be assembled into peptidyl olefins by a variety of reactions. They include an electrophilic aldehyde and nucleophilic sulfone, phosphonium salt, phosphonate, and diselenide. Key enzymatic hydrolysis of prochiral diesters to the corresponding hydroxy esters introduces optical activity. The sequence of the subsequent chemical reactions, either protection- hydrolysis-functionalization or functionalization-hydrolysis- protection, determines the absolute stereochemistry of the final building blocks.
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.
