2-Alkyl-2-carboxy-azetidines as scaffolds for the induction of γ-turns

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• 作者：José ; Luis Baeza ; Guillermo Gerona-Navarro ; M Jesú ; s Pé ; rez de Vega ; M Teresa Garcí ; a-Ló ; pez ; Rosario Gonzá ; lez-Muñ ; iz ; Mercedes Martí ; n-Martí ; nez
• 关键词：Azetidines ; Restricted amino acids ; Peptidomimetics ; Reverse turns
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：21 May 2007
• 卷：48
• 期：21
• 页码：3689-3693
• 文件大小：216 K

摘要

To investigate the ability of 2-alkyl-2-carboxy-azetidines (Azx) to induce reverse turns when incorporated into peptides, RCO-Azx-l-Ala-NHMe dipeptide derivatives were selected as simplified tetrapeptide models, in which the azetidine residue is incorporated at the i + 1 position. Molecular modelling, ¹H NMR and FTIR studies showed the high tendency of the model tetrapeptides to adopt γ-turn conformations, indicating that these azetidine-containing amino acids could serve as general γ-turn promoters.