Synthesis, screening, and sequencing of cysteine-rich one-bead one-compound peptide libraries

Journal of Combinatorial Chemistry

Volumn 10, Issue 5, 2008, Pages 726-731

  Juskowiak, Gary L ^a   McGee, Christopher J ^a   Greaves, John ^a   Van Vranken, David L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYANOGEN BROMIDE; CYSTEINE; DRUG DERIVATIVE; MICROSPHERE; PEPTIDE; PEPTIDE LIBRARY; RESIN;

ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; SYNTHESIS;

ALKYLATION; AMINO ACID SEQUENCE; AMINO ACIDS; CHROMATOGRAPHY, LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; CYANOGEN BROMIDE; CYSTEINE; MASS SPECTROMETRY; MICROSPHERES; PEPTIDE LIBRARY; PEPTIDES; RESINS, SYNTHETIC;

EID: 53049106923     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc800087y     Document Type: Article

References (61)

1. Griffin, B. A.; Adams, S. R.; Tsien, R. Y. Science 1998, 281, 269-72.
2. (a) Rauser, W. E. Methods Enzymol. 1991, 205, 319-333.
3. (b) McIntyre, T. Adv. Biochem. Eng. Biotechnol. 2003, 78, 97-123.
4. (c) Meagher, R. B. Curr. Opin. Plant Bio. 2000, 3, 153-162.
5. (d) Mejare, M.; Bulow, L. Trends Biotechnol. 2001, 19, 67-73.
6. (e) Malachowski, L.; Stair, J. L.; Holcombe, J. A. Pure Appl Chem. 2004, 76, 777-787.
7. Chen, B.; Cao, H.; Yan, P.; Mayer, M. U.; Squier, T. C. Bioconjugate Chem. 2007, 18, 1259-1265.
8. Martin, B. R.; Giepmans, B. N. G.; Adams, S. R.; Tsien, R. Y. Nat. Biotechnol. 2005, 23, 1308-1314.
9. Mejare, M.; Ljung, S.; Bulow, L. Protein Eng. 1998, 11, 489-494.
10. (a) Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84.
11. (b) Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411-448.
12. (c) Kodadek, T.; Bachhawat-Sikder, K. Mol. BioSyst. 2006, 2, 25-35.
13. Angell, Y. M.; Alsina, J.; Albericio, F.; Barany, G. J. Peptide. Res. 2002, 60 (5), 292-299.
14. (a) Gambee, J. E.; Andrews, P. C.; Grant, G. A.; Merrill, B.; Mische, S. M.; Rush, J. Assignment of cysteine and tryptophan residues during protein sequencing: results of ABRF-94SEQ. In Techniques in Protein Chemistry VI; Crabb, J. W., Ed.; Academic Press: San Diego, CA, 1995; pp 209-217.
15. (b) Brune, D.; Denslow, N. D.; Kobayashi, R.; Lane, W. S.; Leone, J. W.; Madden, B. J.; Neveu, J. M.; Pohl, J. J. Biomol. Tech. 2006, 17, 308-326.
16. Stair, J. L.; White, B. R.; Rowland, A.; Holcombe, J. A. J. Comb. Chem. 2006, 8, 929-934.
17. (a) Brenner, S.; Lerner, R. A. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5381-5383.
18. (b) Scheuermann, J.; Dumelin, C. E.; Melkko, S.; Neri, D. J. Biotechnol. 2006, 126, 568-581.
19. (c) Ohlmeyer, M. H. J.; Swanson, R. N.; Dillard, L.; Reader, J. C.; Asouline, G.; Kobayashi, R.; Wigler, M.; Still, W. C. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 10922-10926.
20. (d) Nikolaiev, V.; Stierandova, A.; Krchnak, V.; Seligmann, B.; Lam, K. S.; Salmon, S. E.; Lebl, M. Pep. Res. 1993, 6, 161-70.
21. (e) Song, A.; Zhang, J.; Lebrilla, C. B.; Lam, K. S. J. Am. Chem. Soc. 2003, 125, 6180-6188.
22. Phytochelatin is the best known example of a cadmium-binding peptide and contains gamma amino acids. Cobbett, C. S. Plant Physiol. 2000, 123, 825-832.
23. (a) St.; Hilaire, P. M.; Alves, L. C.; Herrera, F.; Renil, M.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Juliano, M. A.; Juliano, L.; Arevalo, J.; Meldal, M. J. Med. Chem. 2002, 45, 1971-1982.
24. (b) Meldal, M.; Svendsen, I.; Juliano, L.; Juliano, M.; Del Nery, E.; Scharfstein, J. J. Peptide Sci. 1999, 4, 83-91.
25. (c) St. Hilaire, P. M.; Willert, M.; Juliano, M.; Juliano, L.; Meldal, M. J. Comb. Chem. 1999, 1, 509-523.
26. (d) Alves, F. M.; Hirata, I. Y.; Gouvea, I. E.; Alves, M. F.; Meldal, M.; Bromme, D.; Juliano, L.; Juliano, M. A. J. Comb. Chem. 2007, 9, 627-634.
27. (a) Chait, B. T.; Wang, R.; Beavis, R. C.; Kent, S. B. H. Science 1993, 262, 89-92.
28. (b) Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906.
29. (c) Pastor, J. J.; Lingard, I.; Bhalay, G.; Bradley, M. J. Comb. Chem. 2003, 5, 85-90.
30. (d) Tornoe, C. W.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H.; Meldal, M. J. Comb. Chem. 2004, 6, 312-324.
31. Partial Edman sequencing is particularly powerful for peptides composed of α-amino acids, (a) Wang, P.; Arabaci, G.; Pei, D. J. Comb. Chem 2001, 3, 251-254.
32. (b) Sweeney, M. C.; Pei, D. J. Comb. Chem. 2003, 5, 218-222.
33. (c) Thakkar, A.; Wavreille, A.-S.; Pei, D. Anal. Chem. 2006, 78, 5935-5939.
34. (d) Joo, S. H.; Xiao, Q.; Ling, Y.; Gopishetty, B.; Pei, D. J. Am. Chem. Soc. 2006, 128, 13000-13009.
35. (a) Aebersold, R.; Mann, M. Nature 2003, 422, 198-207.
36. (b) Steen, H.; Mann, M. Nat. Rev. Mol. Cell Biol. 2004, 5, 699-711.
37. (c) Biemann, K. Methods Enzymol. 1990, 193, 455-479.
38. Krchnak, V.; Weichsel, A. S.; Issakova, O.; Lam, K. S.; Lebl, M. Mol. Div. 1995, 177-182.
39. (a) Brummel, C. L.; Lee, I. N. W.; Zhou, Y.; Benkovic, S. J.; Winograd, N. Science 1994, 264, 399-402.
40. (b) Biederman, K. J.; Lee, H.; Haney, C. A.; Kaczmarek, M.; Buettner, J. A. J. Pep. Res. 1999, 53, 234-243.
41. (c) Buettner, J. A.; Dadd, C. A.; Hammond, D. J.; Baumbach, G. A. Fibrinolysis 1996, 10 (4), 2.
42. (a) Blom, K. F.; Combs, A. P.; Rockwell, A. L.; Oldenburg, K. R.; Zhang, J. H.; Chen, T. M. Rapid Commun. Mass Spec. 1998, 12, 1192-1198.
43. (b) Vanhoenacker, G.; Liu, L.; Lynen, F.; Madder, A.; De Clercq, P.; Sandra, P. J. Sep. Sci. 2002, 25, 671-676.
44. (c) Redman, J. E.; Wilcoxen, K. M.; Ghadiri, M. R. J. Comb. Chem. 2003, 5, 33-40.
45. (d) Kritzer, J. A.; Luedtke, N. W.; Harker, E. A.; Schepartz, A. J. Am. Chem. Soc. 2005, 127, 14584-14585.
46. (e) Camped, S. A.; Marani, M. M.; Iannucci, N. B.; Côté, S.; Albericio, F.; Cascone, O. Tetrahedron Lett. 2005, 46, 1561-1564.
47. (f) Marani, M. M.; Oliveira, E.; Cote, S.; Camperi, S. A.; Albericio, F.; Cascone, O. Anal Biochem. 2007, 370, 215-222.
48. Paulick, M. G.; Hart, K. M.; Brinner, K. M.; Tjandra, M.; Charych, D. H.; Zuckermann, R. N. J. Comb. Chem. 2006, 8, 417-426.
49. Boysen, R. I.; Hearn, M. T. W. J. Biochem. Biophys. Meth. 2000, 45, 157-168.
50. Lukszo, J.; Patterson, D.; Albericio, F.; Kates, S. A. Lett. Peptide Sci. 1996, 3, 157-166.
51. Spain, S. M.; Rabenstein, D. L. Anal. Chem. 2003, 75, 3712-3719.
52. Angell, Y. M.; Alsina, J.; Albericio, F.; Barany, G. J. Peptide. Res. 2002, 60 (5), 292-299.
53. (a) Kaiser, T.; Nicholson, G. J.; Kohlbau, H. J.; Voelter, W. Tetrahedron Lett. 1996, 37, 1187-1190.
54. (b) White, P.; Dörner, B. Synthesis Notes. In 2006/2007 NovaBiochem Catalog; EMD Biosciences: San Diego, CA, 2006; pp 3.1-3.40.
55. Macmillan, D.; Arham, L. J. Am. Chem. Soc. 2004, 126, 9530-9531.
56. A Microsoft Excel spreadsheet for calculating y- and b-ion masses is included with the Supporting Information.
57. Adams, S. R.; Campbell, R. E.; Gross, L. A.; Martin, B. R.; Walkup, G. K.; Yao, Y.; Llopis, J.; Tsien, R. Y. J. Am. Chem. Soc. 2002, 124, 6063-6076.
58. Alberts, B.; Johnson, A.; Lewis, J.; Raff, M.; Roberts, K.; Walter, P. Molecular Biology of the Cell, 5th ed.; Garland Science: New York, 2008; p 652.
59. 2OH.
60. (a) Silverstein, K. A. T.; Moskal, W. A., Jr.; Wu, H. C.; Underwood, B. A.; Graham, M. A.; Town, C. D.; Vanden-Bosch, K. A. Plant J. 2007, 51, 262-280.
61. (b) Frankel, A. D.; Chen, L.; Cotter, R. J.; Pabo, C. O. Proc. Natl. Acad. Sci. 1988, 85, 6297-6300.