Laboratory of Functional Chemo-Systems and §Laboratory V-SAT (CAMB UMR 7199, CNRS), Labex Medalis, University of Strasbourg , 74 Route du Rhin, 67401 Illkirch-Graffenstaden, France.
Bioconjug Chem. 2014 Feb 19;25(2):202-6. doi: 10.1021/bc400469d. Epub 2014 Jan 16.
Exquisite chemoselectivity for cysteine has been found for a novel class of remarkably hydrolytically stable reagents, 3-arylpropiolonitriles (APN). The efficacy of the APN-mediated tagging was benchmarked against other cysteine-selective methodologies in a model study on a series of traceable amino acid derivatives. The selectivity of the methodology was further explored on peptide mixtures obtained by trypsin digestion of lysozyme. Additionally, the superior stability of APN-cysteine conjugates in aqueous media, human plasma, and living cells makes this new thiol-click reaction a promising methodology for applications in bioconjugation.
新型 3-芳基丙二腈（APN）类试剂具有对半胱氨酸的高度化学选择性，该试剂具有显著的水解稳定性。在对一系列可追踪氨基酸衍生物的模型研究中，将 APN 介导的标记与其他半胱氨酸选择性方法进行了基准测试。该方法的选择性在通过溶菌酶胰蛋白酶消化获得的肽混合物上进一步进行了探索。此外，APN-半胱氨酸缀合物在水介质、人血浆和活细胞中的优越稳定性使这种新的硫醇点击反应成为生物缀合应用中很有前途的方法。
