Selective Irreversible Chemical Tagging of Cysteine with 3-Arylpropiolonitriles
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- 作者：Oleksandr Koniev ; Geoffray Leriche ; Marc Nothisen ; Jean-Serge Remy ; Jean-Marc Strub ; Christine Schaeffer-Reiss ; Alain Van Dorsselaer ; Rachid Baati ; Alain Wagner
- 刊名：Bioconjugate Chemistry
- 出版年：2014
- 出版时间：February 19, 2014
- 年：2014
- 卷：25
- 期：2
- 页码：202-206
- 全文大小：284K
- ISSN：1520-4812
文摘
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鈥揷ysteine conjugates in aqueous media, human plasma, and living cells makes this new thiol-click reaction a promising methodology for applications in bioconjugation.