Wavelength-Selective Photoactivatable Protecting Groups for Thiols
Wavelength-Selective Photoactivatable Protecting Groups for Thiols
复制标题
DOI：
10.1021/ja907287n
复制
发表时间：
2009-11-25
影响因子：
15
通讯作者：
Hagen, Volker
中科院分区：
文献类型：
--
作者：
Kotzur, Nico;Briand, Benoit;Hagen, Volker
我们开发并表征了基于2-硝基苄基和(香豆素-4-基)甲基发色团的硫醇高效、极易溶于水的光致保护基团，其中包括两个新的基团。保护基团由于其不同的吸收极大值，允许以硫醇功能保护的半胱氨酸衍生物的二元混合物与不同的耐光性保护基团通过光照射进行波长选择性光裂解。这一概念也具有功能性，在模型多肽Resact的衍生物中有两个不同的S保护的半胱氨酸残基。Ac-0-Cys(1)(BCMACMOC)、Cys(8)(7，8BCMCMOC)-Resact和Ac-0-Cys(1)(C4MNB)、Cys(8)(BCMACMOC)-分别用波长为402 nm或436 nm的光照射，然后在波长为325 nm处照射，可实现选择性光解。
We developed and characterized efficient, remarkably water-soluble photolabile protecting groups for thiols based on 2-nitrobenzyl and (coumarin-4-yl)methyl chromophores, among them two new ones. The protecting groups allow, due to their different absorption maxima, wave length-selective photocleavage of binary mixtures of cysteine derivatives protected at the thiol function with various photolabile protecting groups by irradiation with light. The concept was also functional with the two different S-protected cysteine residues in derivatives of the model peptide resact. Selective photolysis could be achieved for the peptides Ac-0-Cys(1)(BCMACMOC), Cys(8)(7,8BCMCMOC)-resact and Ac-0-Cys(1)(C4MNB),Cys(8)(BCMACMOC)-resact by irradiation with light of >= 402 nm or >= 436 nm wavelength, respectively, followed by irradiation at lambda >= 325 nm.