Issue 19, 2011

Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides

Abstract

Mild, efficient and racemization-free synthesis of N-protected α, β-unsaturated γ-amino esters with unprecedented high E- stereoselectivity is described. This method is found to be compatible with Boc-, Fmoc- and other side chain protecting groups. The crystal conformations of the vinylogous γ-amino esters in monomers and in homo- and mixed dipeptides are studied. Further, the vinylogous homo-dipeptide showed a β-sheet conformation, while mixed α- and α,β-unsaturated γ-hybrid dipeptide adapted an irregular structure in single crystals.

Graphical abstract: Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides

Supplementary files

Article information

Article type
Paper
Submitted
10 May 2011
Accepted
27 Jun 2011
First published
27 Jun 2011

Org. Biomol. Chem., 2011,9, 6566-6574

Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides

S. M. Mali, A. Bandyopadhyay, S. V. Jadhav, M. G. Kumar and H. N. Gopi, Org. Biomol. Chem., 2011, 9, 6566 DOI: 10.1039/C1OB05732D

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