单线态氧诱导的呋喃氧化用于位点特异性和化学选择性肽连接

Singlet Oxygen-Induced Furan Oxidation for Site-Specific and Chemoselective Peptide Ligation.

作者信息

Antonatou Eirini, Hoogewijs Kurt, Kalaitzakis Dimitris, Baudot Andreas, Vassilikogiannakis Georgios, Madder Annemieke

机构信息

Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Gent, Belgium.

Medical Research Council Laboratory of Molecular Biology, Cambridge, UK.

出版信息

Chemistry. 2016 Jun 13;22(25):8457-61. doi: 10.1002/chem.201601113. Epub 2016 Apr 26.

DOI:10.1002/chem.201601113

PMID:27113264

Abstract

A novel chemoselective ligation methodology has been developed for the facile construction of peptide-based fluorescent probes. Furan-containing peptides were activated by singlet oxygen and covalently engaged by nitrogen nucleophiles to yield stable conjugates. Singlet oxygen was compatible with sensitive amino acid residues within the peptides and a range of fluorophores, bearing different functionalities, were successfully incorporated, illustrating the broad scope of the developed strategy.

摘要

一种新型的化学选择性连接方法已被开发出来，用于简便地构建基于肽的荧光探针。含呋喃的肽被单线态氧激活，并与亲核氮试剂发生共价结合，生成稳定的共轭物。单线态氧与肽内的敏感氨基酸残基兼容，并且成功地引入了一系列具有不同功能的荧光团，这说明了所开发策略的广泛适用性。