"Click chemistry" in the preparation of porous polymer-based particulate stationary phases for μ-HPLC separation of peptides and proteins

Analytical Chemistry

Volumn 78, Issue 14, 2006, Pages 4969-4975

  Slater, Michael ^a   Snauko, Marian ^a,c   Svec, Frantisek ^a,b   Fréchet, Jean M J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^c POLYMER INSTITUTE   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION; PEPTIDES; SOYBEAN TRYPSIN INHIBITOR; STATIONARY PHASES;

ACRYLIC MONOMERS; CATALYSIS; COPOLYMERIZATION; HYDROCARBONS; POLYMERS; REACTION KINETICS;

PROTEINS;

ACRYLIC ACID; ALIPHATIC COMPOUND; ALKYL GROUP; ALKYNE; AZIDE; COPOLYMER; COPPER; ETHYLENE GLYCOL DIMETHACRYLATE; GLYCIDYL METHACRYLATE; LIGAND; METHACRYLIC ACID; METHACRYLIC ACID DERIVATIVE; N (4 PENTYNOYLOXY)SUCCINIMIDE; PEPTIDE; POLYSTYRENE; PROTEIN; SORBENT; SOYBEAN TRYPSIN INHIBITOR; SUCCINIMIDE DERIVATIVE; TRIAZOLE DERIVATIVE; TRYPSIN; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMISTRY; CLICK CHEMISTRY; CYCLOADDITION; EVALUATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGAND BINDING; PEPTIDE ANALYSIS; PHASE SEPARATION; POLYMERIZATION; POROSITY; PRODUCT DEVELOPMENT; PROTEIN ANALYSIS; REVERSED PHASE LIQUID CHROMATOGRAPHY; STATIONARY PHASE;

ALKYNES; AZIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; HYDROPHOBICITY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; POLYMERS; PROTEIN STRUCTURE, TERTIARY; PROTEINS; TRYPSIN;

EID: 33746260321     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac060006s     Document Type: Article

References (42)

1. Svec, F.; Hradil, J.; Coupek, J.; Kalal, J. Angew. Makromol. Chem. 1975, 48, 135-143.
2. Turkova, J.; Blaha, K.; Malanikova, M.; Vancurova, J.; Svec, F.; Kalal, J. Biochim. Biophys. Acta 1978, 524, 162.
3. Ageev, A. N.; Aratskova, A. A.; Belyakova, L. D.; Gvozdich, T. N.; Kiselev, A. V.; Yashin, Y. I.; Kalal, J.; Svec, F. Chromatogrophia 1983, 17, 545-548.
4. Tennikova, T. B.; Horak, D.; Svec, F.; Kolar, J.; Coupek, J.; Trushin, S. V.; Maltsev, A. G.; Belenkii, B. G. J. Chromatogr. 1988, 435, 357-362.
5. Tennikova, T. B.; Horak, D.; Svec, F.; Tennikov, M. B.; Kever, E. E.; Belenkii, B. G. J. Chromatogr. 1989, 457, 187-194.
6. Mal'tsev, V. G.; Nasledov, D. G.; Trushin, S. A.; Tennikova, T. B.; Vinogradova, L. V.; Volokitina, I. N.; Zgonnik, V. N.; Belenkii, B. G. J. High Resolut. Chromatogr. 1990, 13, 185-192.
7. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
8. Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113-2116.
9. Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2110-2113.
10. Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057.
11. Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem 2005, 44, 2210-2215.
12. Wang, Q.; Chittaboina, S.; Barnhill, H. N. Lett. Org. Chem. 2005, 2, 293-301.
13. Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687.
14. Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546.
15. Speers, A. E.; Cravatt, B. F. ChemBioChem 2004, 5, 41-47.
16. Speers, A. E.; Cravatt, B. F. J. Am. Chem. Soc. 2005, 127, 10018-10019.
17. Evans, M. J.; Saghatelian, A.; Sorensen, E. J.; Cravatt, B. F. Nat. Biotechnol. 2005, 23, 1303-1307.
18. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046-15047.
19. Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165.
20. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
21. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Fréchet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928-3932.
22. Helms, B.; Mynar, J. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2004, 126, 15020-15021.
23. Gao, H.; Louche, G.; Sumerlin, B. S.; Jahed, N.; Golas, P.; Matyjaszewski, K. Macromolecules 2005, 38, 8979-8982.
24. Malkoch, M.; Thibault, R. J.; Drockenmuller, E.; Messerschmidt, M.; Voit, B.; Russell, T. P.; Hawker, C. J. J. Am. Chem. Soc. 2005, 127, 14942-14949.
25. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
26. Punna, S.; Kuzelka, J.; Wang, Q.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2215-2220.
27. Löber, S.; Gmeiner, P. Tetrahedron 2004, 60, 8699-8702.
28. Lober, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753-1755.
29. Punna, S.; Kaltgrad, E.; Finn, M. G. Bioconjugate Chem. 2005, 16, 1536-1541.
30. Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413-414.
31. Smigol, V.; Svec, F. J. Appl. Polym. Sci. 1992, 45, 1439-1448.
32. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855.
33. Huisgen, R.; Szeimies, G.; Moebius, L. Chem. Ber. 1967, 100, 2494-2507.
34. Smigol, V.; Svec, F. J. Appl. Polym. Sci. 1992, 46, 1439-1448.
35. Poole, C. F. The Essence of Chromatograph; Elsevier: Amsterdam, 2003; p 281.
36. Rimmer, C. A.; Sander, L. C.; Wise, S. A.; Dorsey, J. G. J. Chromatogr., A 2003, 1007, 11-20.
37. Sander, L. C.; Wise, S. A. J. Sep. Sci. 2003, 26, 283-294.
38. Rimmer, C. A.; Sander, L. C.; Wise, S. A. Anal. Bioanal. Chem. 2005, 382, 698-707.
39. Wilson, N. S.; Gilroy, J.; Dolan, J. W.; Snyder, L. R. J. Chromatogr., A 2004, 1026, 91-100.
40. Euerby, M. R.; Petersson, P. J. Chromatogr., A 2005, 1088, 1-15.
41. Silva, C. R.; Jardim, I. C. S. F.; Airoldi, C. J. Chromatogr., A 2003, 987, 127-138.
42. Rohr, T.; Hilder, E. F.; Donovan, J. J.; Svec, F.; Fréchet, J. M. J. Macromolecules 2003, 36, 1677-1684.