Selective Derivatization of N-Terminal Cysteines Using Cyclopentenediones
作者： Omar Brun , Jordi Agramunt , Lluis Raich , Carme Rovira , Enrique Pedroso
DOI: 10.1021/ACS.ORGLETT.6B02301
关键词:
摘要: The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on thiol. Stable compounds with two fused rings were formed upon 1,2-aminothiols (such as N-terminal cysteines in peptides). Other gave reversibly adducts that equilibrium starting materials. This differential reactivity allows differently placed to be distinguished has been exploited prepare bioconjugates incorporating or three different moieties.
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sci-hub.se 参考文章(51)
Thomas J. Tolbert, Chi-Huey Wong, New Methods for Proteomic Research: Preparation of Proteins with N-Terminal Cysteines for Labeling and Conjugation This research was supported by the NIH (R37 GM44154). Angewandte Chemie International Edition. ,vol. 41, pp. 2171- 2174 ,(2002) , 10.1002/1521-3773(20020617)41:12<2171::AID-ANIE2171>3.0.CO;2-Q
Ramiz I. Nathani, Paul Moody, Vijay Chudasama, Mark E. B. Smith, Richard J. Fitzmaurice, Stephen Caddick, A novel approach to the site-selective dual labelling of a protein via chemoselective cysteine modification. Chemical Science. ,vol. 4, pp. 3455- 3458 ,(2013) , 10.1039/C3SC51333E
Paul Moody, Vijay Chudasama, Ramiz I. Nathani, Antoine Maruani, Stephen Martin, Mark E. B. Smith, Stephen Caddick, A rapid, site-selective and efficient route to the dual modification of DARPins Chemical Communications. ,vol. 50, pp. 4898- 4900 ,(2014) , 10.1039/C4CC00053F
Stephen C. Alley, Dennis R. Benjamin, Scott C. Jeffrey, Nicole M. Okeley, Damon L. Meyer, Russell J. Sanderson, Peter D. Senter, Contribution of linker stability to the activities of anticancer immunoconjugates. Bioconjugate Chemistry. ,vol. 19, pp. 759- 765 ,(2008) , 10.1021/BC7004329
Wen Tang, Matthew L. Becker, "Click" reactions: a versatile toolbox for the synthesis of peptide-conjugates Chemical Society Reviews. ,vol. 43, pp. 7013- 7039 ,(2014) , 10.1039/C4CS00139G
Le-Thu T. Nguyen, M. Talha Gokmen, Filip E. Du Prez, Kinetic comparison of 13 homogeneous thiol–X reactions Polymer Chemistry. ,vol. 4, pp. 5527- 5536 ,(2013) , 10.1039/C3PY00743J
Li-Ya Niu, Ying-Shi Guan, Yu-Zhe Chen, Li-Zhu Wu, Chen-Ho Tung, Qing-Zheng Yang, BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine Journal of the American Chemical Society. ,vol. 134, pp. 18928- 18931 ,(2012) , 10.1021/JA309079F
R. L. Juliano, Xin Ming, Osamu Nakagawa, The chemistry and biology of oligonucleotide conjugates. Accounts of Chemical Research. ,vol. 45, pp. 1067- 1076 ,(2012) , 10.1021/AR2002123
Dmitry A. Stetsenko, Michael J. Gait, Efficient conjugation of peptides to oligonucleotides by "native ligation". Journal of Organic Chemistry. ,vol. 65, pp. 4900- 4908 ,(2000) , 10.1021/JO000214Z
Lianshan Zhang, James P. Tam, Thiazolidine formation as a general and site-specific conjugation method for synthetic peptides and proteins. Analytical Biochemistry. ,vol. 233, pp. 87- 93 ,(1996) , 10.1006/ABIO.1996.0011