Allene Functionalized Azobenzene Linker Enables Rapid and Light-Responsive Peptide Macrocyclization
Allene Functionalized Azobenzene Linker Enables Rapid and Light-Responsive Peptide Macrocyclization
复制标题
DOI：
10.1021/acs.bioconjchem.6b00026
复制
发表时间：
2016-03-01
影响因子：
4.7
通讯作者：
Derda, Ratmir
中科院分区：
文献类型：
--
作者：
Jafari, Mohammad R.;Lakusta, Jenner;Derda, Ratmir
在这篇论文中，我们描述了高效合成双烯丙酰胺官能化的水溶性偶氮苯试剂(BSBDA)，并将其作为一种新的工具来快速生成可见光响应的大环肽和展示在噬菌体表面的肽库。与已建立的含有偶氮苯的卤代烷相比，尿囊酰胺官能团可以促进模型多肽和噬菌体上展示的半胱氨酸的连接，其速度要快2-3个数量级。
In this manuscript, we describe the efficient synthesis of a bis(allenamide) functionalized water-soluble azobenzene reagent (BSBDA) and its application as a new tool for the rapid generation of visible light-responsive macrocyclic peptides and peptide libraries displayed on the surface of bacteriophage. The allenamide functionality promotes cysteine ligation in model peptides and those displayed on phage with rates 2-3 orders of magnitude faster than the established alkyl halide containing azobenzenes.