气炸了：类肽折叠体的构象导向大环化

Fit to be tied: conformation-directed macrocyclization of peptoid foldamers.

作者信息

Holub Justin M, Jang Hangjun, Kirshenbaum Kent

机构信息

Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003-6688, USA.

出版信息

Org Lett. 2007 Aug 16;9(17):3275-8. doi: 10.1021/ol071169l. Epub 2007 Jul 18.

DOI:10.1021/ol071169l

PMID:17637027

Abstract

Covalent macrocyclic constraints can be readily installed on N-substituted glycine "peptoid" oligomer substrates. Cu(I)-catalyzed [3+2] cycloaddition reactions were conducted on solid support to ligate peptoid side chain azide and alkyne functionalities. Intramolecular macrocycle formation is facilitated by preorganizing the reactive groups across one turn of the helical secondary structure. These results confirm that conformational ordering can be exploited to assist the macrocyclization of folded oligomers.

摘要

共价大环约束可以很容易地安装在N-取代甘氨酸“类肽”低聚物底物上。在固体支持物上进行Cu(I)催化的[3+2]环加成反应，以连接类肽侧链叠氮化物和炔烃官能团。通过在螺旋二级结构的一圈中预组织反应基团，促进分子内大环的形成。这些结果证实，可以利用构象有序性来辅助折叠低聚物的大环化。