Oxyazapeptides: Synthesis, Structure Determination, and Conformational Analysis

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• 作者：Suvendu Biswas ; Nader E. Abo-Dya ; Alexander Oliferenko ; Amir Khiabani ; Peter J. Steel ; Khalid A. Alamry ; Alan R. Katritzky
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：78
• 期：17
• 页码：8502-8509
• 全文大小：422K
• 年卷期：v.78,no.17(September 6, 2013)
• ISSN：1520-6904

文摘

Herein we report the synthesis, X-ray structure determination, and conformational analysis of a novel class of heteroatom-modified peptidomimetics, which we shall call 鈥渙xyazapeptides鈥? Substituting the typical native N-C^伪 bond with an O-N^伪 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-N^伪 bond in oxyazapeptides is five times lower than that around the N-N^伪 bond in azapeptides. Also, conformational analysis supported by X-ray suggests that the oxyaza moiety can effectively induce 尾-turns, which can make the newly discovered oxyazapeptide scaffold a useful tool for drug discovery and for design of biologics.