Combinatorial peptide libraries: Robotic synthesis and analysis by nuclear magnetic resonance, mass spectrometry, tandem mass spectrometry, and high-performance capillary electrophoresis techniques

Analytical Biochemistry

Volumn 234, Issue 2, 1996, Pages 126-141

  Boutin, Jean A ^a   Hennig, Philippe ^a   Lambert, Pierre Hervé ^a   Bertin, Sophie ^a   Petit, Laurence ^a   Mahieu, Jean Pierre ^a   Serkiz, Bernard ^a   Volland, Jean Paul ^a   Fauchère, Jean Luc ^a  

^a INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CAPILLARY ELECTROPHORESIS; LIBRARIES; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; ROBOTICS;

ANALYTICAL INVESTIGATIONS; CHARGE-REMOTE FRAGMENTATION; COMBINATORIAL LIBRARY; COMBINATORIAL PEPTIDE LIBRARIES; FAST ATOM BOMBARDMENT; HIGH PERFORMANCE CAPILLARY ELECTROPHORESIS; TANDEM MASS SPECTROMETRY; TWO-DIMENSIONAL NMR;

NUCLEAR MAGNETIC RESONANCE;

AMINO ACID; ARGININE; PEPTIDE; PHENYLALANINE DERIVATIVE;

ARTICLE; CAPILLARY ELECTROPHORESIS; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SYNTHESIS; TANDEM MASS SPECTROMETRY;

EID: 0030056289     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1006/abio.1996.0064     Document Type: Article

References (67)

1. Felder, E. A. (1994) Chimia 48, 531-541.
2. Terrett, N. K., Gardner, M., Gordon, D. W., Kobylecki, R. J., and Steele, J. (1995) Tetrahedron 51, 8235-8173.
3. Geysen, H. M., Rodda, S. J., Mason, T. J., Tribbick, G., and Schoofs, P. G. (1987) J. Immunol. Methods 102, 259-274.
4. Fodor, S. P. A., Read, J. L., Pirrung, M. C., Stryer, L., Lu, A. T., and Solas, D. (1991) Science 251, 767-773.
5. Houghten, R. A. (1993) Gene 137, 7-11.
6. Stankova, M., Wade, S., Lam, K. S., and Lebl, M. (1994) Peptide Res. 7, 292-298.
7. Lam, K. S., Salmon, S. E., Hersh, E. M., Hruby, V. J., Kazmierski, W. M., and Knapp, R. J. (1991) Nature 354, 82-84.
8. Parmley, S. F., and Smith, G. P. (1988) Gene 73, 305-318.
9. Crameri, R., and Suter, M. (1993) Gene 137, 69-75.
10. Winter, J. (1994) Drug Dev. Res. 33, 71-89.
11. Gallop, M. A., Barrett, R. W., Dower, W. J., Fodor, S. P. A., and Gordon, E. M. (1994) J. Med. Chem. 37, 1233-1251.
12. Gordon, E. M., Barrett, R. W., Dower, W. J., Fodor, S. P. A., and Gallop, M. A. (1994) J. Med. Chem. 37, 1385-1401.
13. Houghten, R. A. (1985) Proc. Natl. Acad. Sci. USA 82, 5131-5135.
14. Zuckermann, R. N., Kerr, J. M., Siani, M. A., and Banville, S. C. (1992) Int. J. Peptide Protein Res. 40, 497-506.
15. Andrews, P. C., Boyd, J., Ogorlazek Loo, R., Zhu, C. Q., Grant, K., and Williams, S. (1993) Techniques in Protein Chemistry Academic Press, San Diego.
16. Stevanovic, S., Wiesmuller, K. H., Metzger, J., Beck-Sickinger, G., and Jung, G. (1993) Bioorg. Med. Chem. Lett. 3, 431-436.
17. Metzger, J. W., Wiesmüller, K. H., Gnau, V., Brunjes, J., and Jung, G. (1993) Angew. Chem. 32, 894-896.
18. Brummel, C. L., Lee, I. N., Zhou, Y., Benkovic, S. J., and Winograd, N. (1994) Science 264, 399-402.
19. Youngquist, R. S., Fuentes, G. R., Lacey, M. P., and Keough T. (1995) J. Am. Chem. Soc. 117, 3900-3906.
20. Hortin, G. L., Staatz, W. D., and Santoro, S. A. (1992) Biochem. Int. 26, 731-738.
21. Stevanovic, S., and Jung, G. (1992) Anal. Biochem. 212, 212-220.
22. Busch, K. L., Glish, G. L., and McLuckey, S. A. (1988) MS/MS: Techniques and Applications of Tandem Mass Spectrometry, pp. 248-265, VCH, Weinheim, Germany.
23. Look, G. C., Holmes, C. P., Chinn, J. P., and Gallop, M. A. (1994) J. Org. Chem. 59, 7588-7590.
24. McLaughlin, G. M., Nolan, J. A., Lindahl, J. L., Palmieri, R. H., Anderson, K. W., Morris, S. C., Morrison, J. A., and Bronzert, T. J. (1992) J. Liq. Chromatogr. 15, 961-1021.
25. Deyl, Z., and Struzinsky, R. (1991) J. Chromatogr. 569, 63-122.
26. Wang, S. S. (1973) J. Am. Chem. Soc. 95, 1328-1333.
27. Bax, A., Griffey, R. H., and Hawkins, B. L. (1983) J. Magn. Reson. 55, 30-315.
28. Jung, G., and Beck-Sickinger, A. G. (1992) Angew. Chem. 31, 367-383.
29. Metzger, J. W., Kempter, C., Wiesmüller, K. H., and Jung, G. (1994) Anal. Biochem. 219, 261-277.
30. Naylor, S., Findeis, A. F., Gibson, B. W., and Williams, D. H. (1986) J. Am. Chem. Soc. 108, 6359-6363.
31. Fabris, D., Kelly, M., Murphy, C., Wu, Z. C., and Fenselau, C. (1993) J. Am. Soc. Mass Spectrom. 4, 652-661.
32. Renner, D. R., and Spiteller, G. (1988) Biomed. Mass Spectrom. 15, 75-77.
33. Leary, J. A., Williams, T. D., and Bott, G. (1989) Rapid Commun. Mass Spectrom. 3, 192-196.
34. Tomer, K. B., Deterding, L. J., and Guenat, C. (1991) Biol. Mass Spectrom. 20, 121-129.
35. Teesch, L. M., and Adams, J. (1991) J. Am. Chem. Soc. 113, 812-820.
36. Thorne, G. C., and Gaskell, S. J. (1989) Rapid Commun. Mass Spectrom. 3, 217-221.
37. Kulik, W., Heerma, W., and Terlouw, J. K. (1989) Rapid Commun. Mass Spectrom. 3, 276-278.
38. Blondelle, S. E., Perez-Paya, E., Dooley, C. T., Pinilla, C., and Houghten, R. A. (1995) Trends Anal. Chem. 14, 83-92.
39. Moos, W. H., Green, G. D., and Pavia, M. R. (1993) Annu. Rep. Med. Chem. 28, 315-324.
40. Kurth, M. J., Randall, L. A. A., Chen, C., Melander, C., and Miller, R. B. (1994) J. Org. Chem. 59, 5862-5864.
41. Houghten, R. A., Pinilla, C., Blondelle, S. E., Appel, J. R., Dooley, C. T., and Cuervo, J. H. (1991) Nature 354, 84-86.
42. Boutin, J. A., and Fauchère, A. L. (1996) Trends Pharmacol. Sci. 17, 8-13.
43. Dooley, C. T., and Houghten, R. A. (1993) Life Sci. 52, 1509-1517.
44. Ostresh, J. M., Winkle, J. H., Hamashin, V. T., and Houghten, R. A. (1994) Biopolymers 34, 1681-1688.
45. Songyang, Z., Blechner, S., Hoagland, N., Hoekstra, M. F., Piwnica-Worms, H., and Cantley, L. C. (1994) Curr. Biol. 4, 973-982.
46. Udaka, K., Wiesmüller, K. H., Kienle, S., Jung, G., and Walden, P. (1995) J. Exp. Med. 181, 2097-2108.
47. Kupke, T., Kempter, C., Jung, G., and Götz, F. (1995) J. Biol. Chem. 270, 11282-11289.
48. Pinilla, C., Appel, J. R., Blanc, P., and Houghten, R. A. (1992) BioTechniques 13, 901-905.
49. Pinilla, C., Appel, J. R., and Houghten, R. A. (1994) Biochem. J. 301, 847-853.
50. Pinilla, C., Appel, J., Blondelle, S., Dooley, C., Dörner, B., Eichler, J., Ostresh, J., and Houghten, R. A. (1995) Biopolymers 37, 221-240.
51. Songyang, Z., Shoelson, S. E., Chaudhuri, M., Gish, G., Pawson, T., Haser, W. G., King, F., Roberts, T., Ratnofsky, S., Lechleider, R. J., Neel, B. G., Birge, R. B., Fajardo, J. E., Chou, M. M., Hanafusa, H., Schaffhausen, B., and Cantley, L. C. (1993) Cell 72, 767-778.
52. Songyang, Z., Margolis, B., Chaudhuri, M., Shoelson, S. E., and Cantley, L. C. (1995) J. Biol. Chem. 270, 14863-14866.
53. Freier, S. M., Konings, D. A. M., Wyatt, J. R., and Ecker, D. J. (1995) J. Med. Chem. 38, 344-352.
54. Lyttle, M. H. (1995) Drug Dev. Res. 35, 230-236.
55. Lam, K. S., Wu, J., and Lou, Q. (1995) Int. J. Peptide Protein Res. 45, 587-592.
56. Eichler, J., and Houghten, R. A. (1993) Biochemistry 32, 11035-11041.
57. Wu, J., Ma, Q. N., and Lam, K. S. (1994) Biochemistry 33, 14825-14833.
58. Bianchi, E., Folgori, A., Wallace, A., Nicotra, M., Acalli, S., Phalipon, A., Barbato, G., Bazzo, R., Cortese, R., Felici, F., and Pessi, A. (1995) J. Mol. Biol. 247, 154-160.
59. Ostresh, J. M., Husar, G. M., Blondelle, S. E., Dörner, B., Weber, P. A., and Houghten, R. A. (1994) Proc. Natl. Acad. Sci. USA 91, 11138-11142.
60. Eichler, J., Lucka, A. W., and Houghten, R. A. (1994) Peptide Res. 7, 300-307.
61. Dooley, C. T., Chung, N. N., Wilkes, B. C., Schiller, P. W., Bidlack, J. M., Pasternak, G. W., and Houghten, R. A. (1994) Science 266, 2019-2022.
62. Tegge, W., Frank, R., Hofmann, F., and Dostmann, W. R. G. (1995) Biochemistry 34, 10569-10577.
63. Deprez, B., Williard, X., Bourel, L., Coste, H., Hyafil, F., and Tartar, A. (1995) J. Am. Chem. Soc. 117, 5405-5406.
64. Stankova, M., Wade, S., Lam, K. S., and Lebl, M. (1994) Peptide Res. 7, 292-298.
65. Horwell, D. C., Howson, W., Ratcliffe, G. S., and Rees, D. C. (1993) Bioorg. Med. Chem. Lett. 3, 799-802.
66. Quesnel, A., Casrouge, A., Kourilsky, P., Abastado, J. P., and Trudelle, Y. (1995) Peptide Res. 8, 44-51.
67. Smith, P. W., Lai, J. Y. Q., Whittington, A. R., Cox, B., and Houston, J. G. (1994) Bioorg. Med. Chem. Lett. 4, 2821-2824.