Synthesis and Conformational Studies of Peptidomimetics Containing a New Bifunctional Diketopiperazine Scaffold Acting as a 详细信息    查看全文

• 作者：Ana Sofia M. Ressurreiç ; ã ; o ; Andrea Bordessa ; Monica Civera ; Laura Belvisi ; Cesare Gennari ; Umberto Piarulli
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 18, 2008
• 年：2008
• 卷：73
• 期：2
• 页码：652 - 660
• 全文大小：387K
• 年卷期：v.73,no.2(January 18, 2008)
• ISSN：1520-6904

文摘

A practical synthesis of a new bifunctional diketopiperazine (DKP) scaffold 1, formally derived fromthe cyclization of L-aspartic acid and (S)-2,3-diaminopropionic acid, is reported. DKP-1 bears a carboxylicacid and an amino functionalities in a cis relationship, which have been used to grow peptide sequences.Tetra-, penta-, and hexapeptidomimetic sequences were prepared by solution-phase peptide synthesis(Boc strategy). Conformational analysis of these derivatives was carried out by a combination of ¹HNMR spectroscopy, IR spectroscopy, CD spectroscopy, and computer modeling, and reveals the formationof -hairpin mimics involving 10-membered and 18-membered H-bonded rings and a reverse turn of thegrowing peptide chain.