ChemInform Abstract: Oxyazapeptides: Synthesis, Structure Determination, and Conformation Analysis.

Abstract

Oxyazapeptides: Synthesis, Structure Determination, and Conformation Analysis. -Substituting the typical native N-C α bond with an O-N α bond, completely new, previously unknown peptidomimetics are created, which are hydrolytically stable and display very interesting conformational behavior. Force field calculations reveal that the barrier to rotation around the O-N α bond is five times lower than that around the N-N α bond in azapeptides. It is also shown by conformational analysis that the oxyaza moiety can effectively induce β-turns, which can make the newly discovered oxyazapeptide scaffold a useful tool for drug discovery and to design biologics. -(BISWAS, S.; ABO-DYA, N. E.; OLIFERENKO, A.; KHIABANI, A.; STEEL, P. J.; ALAMRY, K. A.; KATRITZKY*, A. R.; J. Org. Chem. 78 (2013) 17, 8502-8509, http://dx.doi.org/10.1021/jo401234g ; Dep. Chem., Univ. Fla., Gainesville, FL 32611, USA; Eng.) -S. Adam 52-209