Journal of the American Chemical Society
Article
(8) (a) Liu, D.; Xie, Y.; Shao, H.; Jiang, X. Angew. Chem., Int. Ed.
CONCLUSION
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2009, 48, 4406. (b) Minko, S.; Muller, M.; Motornov, M.; Nitschke,
̈
We have developed a facile strategy to realize an on-demand
stepwise modification on surfaces controlled by electro-
chemistry. The initial trimethoxybenzene-terminated SAMs
on gold surface are electroinactive. After an electrochemical
activation process, the SAMs generate a catechol-like redox
center that can react with L-cysteine or L-cysteine-containing
peptide. This reaction can be readily monitored by electro-
chemistry, EC-SERS, and XPS techniques. Then electro-
chemical activation and reaction with L-cysteine for the second
time can be carried out to attach another L-cysteine-containing
peptide. By using our stepwise electrochemical activation
strategy, utilizing L-cysteine as a linkage, we have demonstrated
a switchable surface that can be used to not only immobilize
but also conduct conformation control of bioactive peptide. It is
believed that this simple, efficient, and well-controlled smart
surface may find applications in immobilizing and conformation
control of peptide and protein on surfaces.
M.; Grundke, K.; Stamm, M. J. Am. Chem. Soc. 2003, 125, 3896.
(c) Choi, I.; Kim, Y.-K.; Min, D.-H.; Lee, S.; Yeo, W.-S. J. Am. Chem.
Soc. 2011, 133, 16718. (d) Seo, H.; Choi, I.; Lee, J.; Kim, S.; Kim, D.
E.; Kim, S. K.; Yeo, W. S. Chem.Eur. J. 2011, 17, 5804.
(9) Choi, I. S.; Chi, Y. S. Angew. Chem., Int. Ed. 2006, 45, 4894.
(10) (a) Yeo, W. S.; Yousaf, M. N.; Mrksich, M. J. Am. Chem. Soc.
2003, 125, 14994. (b) Yeo, W. S.; Min, D. H.; Hsieh, R. W.; Greene,
G. L.; Mrksich, M. Angew. Chem., Int. Ed. 2005, 44, 5480. (c) He, X.-
P.; Wang, X.-W.; Jin, X.-P.; Zhou, H.; Shi, X.-X.; Chen, G.-R.; Long,
Y.-T. J. Am. Chem. Soc. 2011, 133, 3649. (d) Hoover, D. K.; Chan, E.
W.; Yousaf, M. N. J. Am. Chem. Soc. 2008, 130, 3280. (e) Yeo, W. S.;
Mrksich, M. Langmuir 2006, 22, 10816. (f) Ma, W.; Li, D.-W.;
Sutherland, T. C.; Li, Y.; Long, Y.-T.; Chen, H.-Y. J. Am. Chem. Soc.
2011, 133, 12366.
(11) Kim, K.; Jeon, W. S.; Kang, J.-K.; Lee, J. W.; Jon, S. Y.; Kim, T.;
Kim, K. Angew. Chem., Int. Ed. 2003, 115, 2395.
(12) Mendes, P. M. Chem. Soc. Rev. 2008, 37, 2512.
(13) (a) White, R. J.; Ervin, E. N.; Yang, T.; Chen, X.; Daniel, S.;
Cremer, P. S.; White, H. S. J. Am. Chem. Soc. 2007, 129, 11766.
(b) Erickson, D.; Liu, X.; Venditti, R.; Li, D.; Krull, U. J. Anal. Chem.
2005, 77, 4000. (c) Du, D.; Zou, Z.; Shin, Y.; Wang, J.; Wu, H.;
Engelhard, M. H.; Liu, J.; Aksay, I. A.; Lin, Y. Anal. Chem. 2010, 82,
2989.
(14) (a) Saha, S.; Flood, A. H.; Stoddart, J. F.; Impellizzeri, S.; Silvi,
S.; Venturi, M.; Credi, A. J. Am. Chem. Soc. 2007, 129, 12159. (b) Luo,
W.; Westcott, N. P.; Pulsipher, A.; Yousaf, M. N. Langmuir 2008, 24,
13096. (c) Westcott, N. P.; Pulsipher, A.; Lamb, B. M.; Yousaf, M. N.
Langmuir 2008, 24, 9237. (d) Love, J. C.; Estroff, L. A.; Kriebel, J. K.;
Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103.
(e) Ulman, A. Chem. Rev. 1996, 96, 1533. (f) Ma, W.; Long, Y. T.
Chem. Soc. Rev. 2013, 43, 30.
ASSOCIATED CONTENT
* Supporting Information
Details of synthesis, XPS of the SAMs and other CVs. This
material is available free of charge via the Internet at http://
■
S
AUTHOR INFORMATION
Corresponding Author
Notes
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(15) Cao, X. Y.; Yang, J.; Dai, F.; Ding, D. J.; Kang, Y. F.; Wang, F.;
Li, X. Z.; Liu, G. Y.; Yu, S. S.; Jin, X. L.; Zhou, B. Chem.Eur. J. 2012,
18, 5898.
(16) Wu, D.-Y.; Li, J.-F.; Ren, B.; Tian, Z.-Q. Chem. Soc. Rev. 2008,
37, 1025.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work is supported by National Basic Research Program of
China (973 Program) No. 2012CB933102, National Natural
Science Foundation of China (NSFC 21233001, 21190034,
21172101), Specialized Research Fund for the Doctoral
Program of Higher Education (SRFDP 20110211130001),
the Fundamental Research Funds for the Central Universities
and 111 Project.
(17) Li, J.; Sun, C. L.; Tan, L.; Xie, Y. L.; Zhang, H. L. Langmuir
2013, 29, 5199.
(18) Nguyen, N. H.; Esnault, C.; Gohier, F.; Bel
C. Langmuir 2009, 25, 3504.
(19) (a) Nasr, B.; Abdellatif, G.; Canizares, P.; Sae
́
anger, D.; Cougnon,
́
z, C.; Justo, L.;
̃
Rodrigo, M. A. Environ. Sci. Technol. 2005, 39, 7234. (b) Mu, S.; Chen,
C. J. Phys. Chem. C 2012, 116, 3065.
(20) Petrangolini, P.; Alessandrini, A.; Berti, L.; Facci, P. J. Am. Chem.
Soc. 2010, 132, 7445.
(21) Cao, K.; Stack, D. E.; Ramanathan, R.; Gross, M. L.; Rogan, E.
G.; Cavalieri, E. L. Chem. Res. Toxicol. 1998, 11, 909.
(22) Napolitano, A.; Panzella, L.; Leone, L.; D’Ischia, M. Acc. Chem.
Res. 2012, 46, 519.
REFERENCES
(1) Milner, S. T. Science 1991, 251, 905.
■
(2) (a) Zhu, M. Q.; Zhu, L.; Han, J. J.; Wu, W.; Hurst, J. K.; Li, A. D.
J. Am. Chem. Soc. 2006, 128, 4303. (b) Rueckes, T.; Kim, K.;
Joselevich, E.; Tseng, G. Y.; Cheung, C. L.; Lieber, C. M. Science 2000,
289, 94. (c) Pease, A. R.; Jeppesen, J. O.; Stoddart, J. F.; Luo, Y.;
Collier, C. P.; Heath, J. R. Acc. Chem. Res. 2001, 34, 433. (d) Lamb, B.
M.; Yousaf, M. N. J. Am. Chem. Soc. 2011, 133, 8870.
(3) (a) Abbott, S.; Ralston, J.; Reynolds, G.; Hayes, R. Langmuir
1999, 15, 8923. (b) Ichimura, K.; Oh, S.-K.; Nakagawa, M. Science
2000, 288, 1624.
(23) Trammell, S. A.; Moore, M.; Schull, T. L.; Lebedev, N. J.
Electroanal. Chem. 2009, 628, 125.
(24) (a) Samanen, J.; Ali, F.; Romoff, T.; Calvo, R.; Sorenson, E.;
Vasko, J.; Storer, B.; Berry, D.; Bennett, D. J. Med. Chem. 1991, 34,
3114. (b) Pfaff, M.; Tangemann, K.; Muller, B.; Gurrath, M.; Muller,
G.; Kessler, H.; Timpl, R.; Engel, J. J. Biol. Chem. 1994, 269, 20233.
(25) Wang, R. L. C.; Kreuzer, H. J.; Grunze, M. J. Phys. Chem. B
1997, 101, 9767.
(4) (a) Weissmuller, J.; Viswanath, R. N.; Kramer, D.; Zimmer, P.;
̈
Wurschum, R.; Gleiter, H. Science 2003, 300, 312. (b) Luk, Y.-Y.;
̈
Abbott, N. L. Science 2003, 301, 623.
(5) (a) Matthews, J. R.; Tuncel, D.; Jacobs, R. M. J.; Bain, C. D.;
Anderson, H. L. J. Am. Chem. Soc. 2003, 125, 6428. (b) Liu, D.;
Bruckbauer, A.; Abell, C.; Balasubramanian, S.; Kang, D. J.;
Klenerman, D.; Zhou, D. J. Am. Chem. Soc. 2006, 128, 2067.
(6) Arotca̧ rena, M.; Heise, B.; Ishaya, S.; Laschewsky, A. J. Am. Chem.
́
Soc. 2002, 124, 3787.
(7) (a) Whitesides, G. M.; Grzybowski, B. Science 2002, 295, 2418.
(b) Lahann, J.; Mitragotri, S.; Tran, T.-N.; Kaido, H.; Sundaram, J.;
Choi, I. S.; Hoffer, S.; Somorjai, G. A.; Langer, R. Science 2003, 299,
371.
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