1452154-06-1Relevant academic research and scientific papers
Oxyazapeptides: Synthesis, structure determination, and conformational analysis
Biswas, Suvendu,Abo-Dya, Nader E.,Oliferenko, Alexander,Khiabani, Amir,Steel, Peter J.,Alamry, Khalid A.,Katritzky, Alan R.
, p. 8502 - 8509 (2013/09/24)
Herein we report the synthesis, X-ray structure determination, and conformational analysis of a novel class of heteroatom-modified peptidomimetics, which we shall call "oxyazapeptides". Substituting the typical native N-Cα bond with an O-Nα bond creates a completely new, previously unknown family of peptidomimetics, which are hydrolytically stable and display very interesting conformational behavior. Force field calculations revealed that the barrier to rotation around the O-Nα bond in oxyazapeptides is five times lower than that around the N-Nα bond in azapeptides. Also, conformational analysis supported by X-ray suggests that the oxyaza moiety can effectively induce β-turns, which can make the newly discovered oxyazapeptide scaffold a useful tool for drug discovery and for design of biologics.
