Surfaces for immobilization of n-terminal cysteine derivatives via native chemical ligation

Langmuir

Volumn 24, Issue 24, 2008, Pages 13962-13968

  Anderson, Sally ^a  

^a SHARP LABORATORIES OF EUROPE LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE BONDS; BUFFER SOLUTIONS; CONCENTRATION OF; COVALENTLY BOUNDS; DENSE MONOLAYERS; DIVERSE APPLICATIONS; ESTER GROUPS; FUNCTIONALIZED; GLASS SURFACES; IMPROVED METHODS; LINEAR RELATIONSHIPS; N TERMINALS; NATIVE CHEMICAL LIGATIONS; NCL REACTIONS; SURFACE FUNCTIONALIZATION; TERMINAL ALKENES; THIOESTER; THIOESTERS; THIOPHENYL; UNDECANOIC ACIDS; WATER CONTACT ANGLES;

ABSORPTION; AMIDES; CHROMOPHORES; CONTACT ANGLE; ESTERIFICATION; ESTERS; GLASS; HYDROSILYLATION; OLEFINS; PLATINUM; SILANES; SULFUR COMPOUNDS; TOLUENE;

ABSORPTION SPECTROSCOPY;

CYSTEINE; DRUG DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SURFACE PROPERTY;

CYSTEINE; MOLECULAR STRUCTURE; SURFACE PROPERTIES;

EID: 61849136152     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la8022024     Document Type: Article

References (37)

1. Schiel, J. E.; Mallik, R.; Soman, S.; Joseph, K. S.; Hage, D. S. J. Sep. Sci. 2006, 29, 719-737.
2. Bertrand, P.; Jonas, A.; Laschewsky, A.; Legras, R. Macromol. Rapid Commun. 2000, 21, 319-348.
3. del Campo, A.; Boos, D.; Spiess, H. W.; Jonas, U. Angew. Chem., Int. Ed. 2005, 44, 4707-4712.
4. Auletta, T.; Dordi, B.; Mulder, A.; Sartori, A.; Onclin, S.; Bruinink, C. M.; Péter, M.; Nijhuis, C. A.; Beijleveld, H.; Schönherr, H.; Vancso, G. J.; Casnati, A.; Ungaro, R.; Ravoo, B. J.; Huskens, J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2004, 43, 369-373.
5. Vilan, A.; Cahen, D. Trends Biotechnol. 2002, 20, 22-29.
6. Ganesan, R.; Yoo, S. Y.; Choi, J.-H.; Lee, S. Y.; Kim, J.-B. J. Mater. Chem. 2008, 18, 703-709.
7. (a) Onclin, S.; Ravoo, B. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2005, 44, 6282-6304.
8. (b) Zhang, C.; Suslick, K. S. J. Am. Chem. Soc. 2005, 127, 11548-11549.
9. MacBeath, G.; Schreiber, S. L. Science 2000, 289, 1760-1763.
10. Woo, Y.-H.; Camarero, J. A. Curr. Nanosci. 2006, 93-103.
11. (a) Köhn, M.; Wacker, R.; Peters, C.; Schröder, H.; Soulère,L.; Breinbauer, R.; Niemeyer, C. M.; Waldmann, H. Angew. Chem., Int. Ed. 2003, 42, 5830-5834.
12. (b) Soellner, M. B.; Dickson, K. A.; Nilsson, B. L.; Raines, R. T. J. Am. Chem. Soc. 2003, 125, 11790-11791.
13. (a) Lesaicherre, M.-L.; Uttamchandani, M.; Chen, G. Y. J.; Yao, S. Q. Bioorg. Med. Chem. Lett. 2002, 12, 2079-2083.
14. (b) Uttamchandani, M.; Chan, E W S. Chen, G. Y. J.; Yao, S. Q. Bioorg. Med. Chem. Lett. 2003, 13, 2997-3000.
15. (c) Girish, A.; Sun, H.; Yeo, D. S. Y.; Chen, G. Y. J.; Chua, T.-K.; Yao. S. Q. Bioorg. Med. Chem. Lett. 2005, 15, 2447-2451.
16. Camarero, J. A.; Kwon, Y.; Coleman,M. A. J. Am. Chem. Soc. 2004, 126, 14730-14731.
17. Wojtyk, J. T. C.; Morin, K. A.; Boukherroub, R.; Wayner, D. D. M. Langmuir 2002, 18, 6081-6087.
18. Houseman, B. T.; Huh, J. H.; Kron, S. J.; Mrksich, M. Nat. Biotechnol. 2002, 20, 270-274.
19. Hergenrother, P. J.; Depew, K. M.; Schreiber, S. L. J. Am. Chem. Soc. 2000, 122, 7849-7850.
20. Barnes-Seeman, D.; Park, S.-B.; Koehler, A. N.; Schreiber, S. L. Angew. Chem., Int. Ed. 2003, 42, 2376-2379.
21. MacBeath, G.; Koehler, A. N.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121. 7967-7968.
22. Devaraj, N. K.; Dinolfo, P. H.; Chidsey, C. E. D.; Collman, J. P. J. Am. Chem. Soc. 2006, 128, 1794-1795.
23. Schmid, E. L.; Keller, T. A.; Dienes, Z.; Vogel, H. Anal. Chem. 1997, 69, 1979-1985.
24. (a) Yeo, D. S. Y.; Srinivasan, R.; Chen, G. Y. J.; Yao, S.Q. Chem-Eur. J. 2004, 10, 4664-4672.
25. (b) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266,776-779.
26. (c) Johnson, E. C. B.; Kent, S. B. H. J. Am. Chem. Soc. 2006, 128, 6640-6646.
27. Helms, B.; van Baal, I.; Merkx, M.; Meijer, E. W. ChemBioChem 2007, 8(15), 1790-1794.
28. Torbeev, V. Y.; Kent, S. B. H. Angew. Chem., Int. Ed. 2007, 46, 1667-1670.
29. Fadeev, A. Y.; McCarthy, T. J. Langmuir 2000, 16, 7268-7274.
30. "Piranha solution" was prepared by carefully adding hydrogen peroxide solution (27%, 20 mL) to concentrated sulfuric acid (45 mL) and used while still warm. Explosive mixtures may form with organic material, so great caution should be taken.
31. Hermanson, G. T. Bioconjugate Techniques; Academic Press, Inc.: San Diego, CA, 1996; Chapter 8.
32. -2. This method assumes that the integrated extinction coefficient (oscillator strength) of lissamine in solution is the same as that of surface-bound lissamine.
33. (b) McCallien, D. W. J.; Burn, P. L.; Anderson, H. L. J. Chem. Soc, Perkin Trans. 1 1997, 2581-2586.
34. 2. At lower functionalization densities, the spectra are too noisy.
35. (a) A 1% solution of Tween 20 has a concentration of 8 mM, significantly higher than its critical micelle concentration (0.08 mM); see.
36. (b) Malik, W. U.; Jhamb, O P. Kolloid. Z Z. Polym. 1970, 242, 1209-1211.
37. For an interesting example of monitoring NCL at a surface see Wieczerzak, E., Hamel, R., Jr.; Chabot, V.; Aimez, V.; Grandbios, M.; Charette, P. G.; Escher, E. Biopolymers, 2008, 90, 415-420.