High Resolution Magic Angle Spinning NMR for Analyzing Small Molecules Attached to Solid Support

Combinatorial Chemistry and High Throughput Screening

Volumn 6, Issue 7, 2003, Pages 741-753

  Schröder, Harald ^a  

^a Aventis Combinatorial Technol Ctr   (United States)

Author keywords

Combinatorial chemistry; Diffusion filter; Dipolar recoupling; High resolution magic angle spinning NMR; HR MAS NMR; Reaction monitoring on bead

Indexed keywords

SOLVENT;

CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; DIFFUSION; FILTER; HIGH RESOLUTION MAGIC ANGLE SPINNING NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVIEW; SOLID; STRUCTURE ANALYSIS;

EID: 0346251242     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620703771981269     Document Type: Review

References (91)

1. Hijfte, L. V., Marciniak, G., Froloff, N. J. Chrom. B, 1999, 725, 3-15.
2. Dulery, B. D., Verne-Mismer J., Wolf E., Kugel C., Van Hijfte L. J. Chrom. B, 1999, 725, 39-47.
3. Broenstrup, M. Top. Curr. Chem., 2003, 225, 283-302.
4. a) Ross, A., Senn, H. DDT, 2001, 6, 583-593.
5. b) Levenberg, M. J. Autom. Chem., 1996, 4, 149-152.
6. c) Ross, A., Schlotterbeck, G., Senn, H., von Kienlin, M. Angew. Chem. Int. Ed., 2001, 40, 3243-3245.
7. a) Spraul, M. Anal. Commun., 1997, 34, 339-341.
8. b) Keifer, P. A., Curr. Opin. Biotechnol. 1999, 10, 34-41.
9. c) Keifer, P. A. J. Comb. Chem., 2000, 2, 151-171.
10. d) Stockman, B. J. Curr. Opin. Drug Discov., 2000, 3, 269-274.
11. a) Hegy, G., Görlach, E., Richmond, R., Bitsch, F. Rapid Commun. Mass Spectrom., 1996, 9, 1894-1900.
12. b) Görlach, E., Richmond, R., Lewis, I. Anal. Chem., 1998, 70, 3227-3234.
13. c) ACD/CombiNMR, Advanced Chemistry Development, Inc., Toronto. (www.acdlabs.com).
14. d) Keifer, P. A., Smallcombe, S. H., Williams, E. H., Salomon, K. E., Mendez, G., Belletire, J. L., Moore, C. D. J. Comb. Chem., 2000, 2, 151-171.
15. e) Kalelkar, S., Dow, E. R., Grimes, J., Clapham, M., Hu, H. J. Comb. Chem., 2002, 4, 622-629.
16. f) Griffiths, L., Bright, J. D. Magn. Reson. Chem., 2002, 40, 623-634.
17. a) Schröder, H., Neidig, P., Rossé, G. Angew. Chem. Int. Ed., 2000, 39, 3816-3819.
18. b) Schroder, H., Neidig, P. 1998, DE-19849231-C2.
19. c) Rossé, G., Neidig, P., Schroeder, H. in Methods in Molecular Biology, Combinatorial Library Methods and Protocols, 2002, Humana Press Inc., Totowa, NJ, 123-139.
20. d) Schröder H., Neidig P. Bruker Report, 1999, 147, 18-21.
21. e) Fischer C., Neidig P., Schröder H. Bruker Report, 2000, 148, 27.
22. a) Shah, N., Gao, M., Tsutsui, K., Lu, A., Davis, J., Scheuerman, R., Fitch, W. L. J. Comb. Chem., 2000, 2, 453-460.
23. b) Fitch, W. L., Szardenings, A. K. Tetrahedron Lett., 1997, 38 (10), 1689-1692.
24. c) Yurek, D. A., Branch, D. L., Kuo, M.-S. J. Comb. Chem., 2002, 4, 138-148.
25. d) Fang, L., Wan, M., Pennacchio, M., Pan, J. J. Comb. Chem., 2000, 2, 254-257.
26. e) Fang, L., Pan, J., Yan, B. Biotechnol. Bioeng. (Comb. Chem.), 2001, 71, 161-171.
27. Girald, D., Rizo, J., Pedroso, E. Tetrahedron, 1984, 40, 4141.
28. Look, G. C., Holmes, C. P., Chinn, J. P., Gallop, M. A. J. Org. Chem. 1994, 59, 7588.
29. Shapiro, M. J., Gounarides, J. S. Prog. NMR Spectr., 1999, 35, 153-200.
30. a) Scicinski, J. J., Congreve, M. S., Kay, C., Ley, S. V. Current Medicinal Chemistry, 2002, 9, 2103-2127.
31. b) Lippens, G., Warrass, R., Wieruszeski, J.-M., Rousselot-Pailley, P., Chessari, G. Comb. Chem. High Throughput Screening, 2001, 4, 333-351.
32. c) Shapiro, M. J., Gounarides, J. S. Biotechnol. Bioeng. (Comb. Chem.), 2000/2001, 71, 130-148.
33. a) Lippens, G., Bourdonneau, M., Dhalluin, C., Warrass, R., Richert, T., Seethraraman, C., Boutillon, C., Piotto, M. Curr. Org. Chem., 1999, 3, 147-169.
34. b) Duus, J. O., Gotfredsen, C. H., Bock, K. Chem. Rev., 2000, 100, 4589-4614.
35. c) Vaino, A. R., Janda, K. D. J. Comb. Chem., 2000, 2, 579-596.
36. de Miguel, Y. R., Shearer, A. S. Biotechnol. Bioeng. (Comb. Chem.), 2001, 71, 119-129.
37. Huber, W., Bubendorf, A., Grieder, A., Obrecht, D. Anal. Chim. Acta, 1999, 393, 213-221.
38. Anderson, R. C., Stokes, J.P., Shapiro, M. J. Tetrahedron Lett., 1995, 36, 5311.
39. Keiffer, P. A. J. Org. Chem., 1996, 61, 1558.
40. Pop, I. E., Dhalluin, C. F., Déprez, B. P., Melnyk, P. C., Lippens, G. M., Tartar, A. L. Tetrahedron, 1996, 52, 12209-12222.
41. Dhalluin, C. F., Boutillon, C., Tartar, A., Lippens, G. M. J. Am. Chem. Soc. 1997, 119, 10494.
42. Jelinek, R., Valente, A. P., Valentine, K. G., Opella, S. J. J. Magn. Reson. 1997, 125, 185.
43. Shapiro, M. J., Chin, J., Marti, R. E., Jarosinski, M. A. Tetrahedron Lett., 1997, 38, 1333.
44. Dhalluin, C. F. Ph.D. Thesis, Université des Sciences et Technologies de Lille, France. 1997.
45. Lowe, J. J. Phys. Rev. Lett. 1959, 2, 285.
46. Andrew, E. R., Bradbury, A., Eades, R. G. Nature, 1958, 182, 1659.
47. Mehring, M. High resolution NMR spectroscopy in solids, Springer: Berlin, 1983.
48. Vanderhart, D. L. Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M., and Harris, R. K. Eds, Wiley & Sons, New York, 1996, vol. 5, 2938-2946.
49. Neuhaus, D., Williamson, M., The nuclear Overhauser effect in structural and conformational analysis, VCH Publishers: Cambridge, 1989.
50. Maas, W. E., Laukien, F. H., Cory, D. G. J. Am. Chem. Soc., 1996, 118, 10385.
51. Walsh, D., Wu, Daqian; Cahng, Y.-T. Curr. Opin. Chem. Biol., 2003, 7, 1-9.
52. Grotli, M., Gotfredsen, C. H., Rademann, J., Buchardt, J., Clark, J. A., Duus, J. O., Meldal, M. J. Comb. Chem., 2000, 2, 108-119.
53. Auzanneau, F.-I., Meldal, M., Bock, K. J. Pept. Sci., 1995, 1, 31-44.
54. Gerritz, S. W., Norman, M. H., Barger, L. A., Berman, J., Bigham, E. C., Bishop, M. J., Drewry, D. H., Garrison, D. T., heyer, D., Hodson, S. J., Kakel, J. A., Linn, J. A., Marron, B. E., Nanthakumar, S. S., Navas, F. J. III J. Comb. Chem., 2003, 5, 110-117.
55. Mimotops, Inc. (www.mimotopes.com)
56. Atrash, B; Bradley, M., Kobylecki, R., Cowell, D., Reader, J. Angew. Chem. Int. Ed., 2001, 40, 938-941.
57. Nicoloau, K. C., Xiao, X.-Y., Parandoosh, Z., Senyei, A., Nova, M. P. Angew. Chem. Int. Ed., 1995, 34, 2289.
58. Houghten, R. A. Proc. Natl. Acad. Sci. USA., 1985, 82, 5131.
59. Bray, A. M., Chiefari, D. S., Valerio, R. M., Maeji, N. J. Tetrahedron Lett., 1995, 36, 5081-5084.
60. Sefler, A. M., Gerritz, S. W. J. Comb. Chem., 2000, 2, 127-133.
61. a) Meissner, A., Bloch, P., Humpfer, E., Spraul, M., Sorensen, O. W. J. Am. Chem. Soc., 1997, 119, 1787-1788.
62. b) Chin, J., Fell, B., Pochapsky, S., Shapiro, M. J., Wareing, J. R. J. Org. Chem., 1998, 63, 1309-1311.
63. c) Tommasi, R. A., Nantermet, P. G., Shapiro, M. J., Chin, J., Brill, W. K.-D., Ang, K. Tetrahedron Lett., 1998, 39, 5477-5480.
64. Warrass, R., Wieruszeski, J.-M., Lippens, G. J. Am. Chem. Soc., 1999, 121, 3787-3788.
65. Shapiro, M. J., Chin, J., Chen, A., Wareing, J. R., Tang, Q., Tommasi, R. A., Marepalli, H. R. Tetrahedron Lett., 1999, 40, 6141-6143.
66. Chin, J. A., Chen, A., Shapiro, M. J. J. Comb. Chem., 2000, 2, 293-296.
67. Fruchart, J.-S., Lippens, G., Kuhn, C., Gras-Masse, H., Melnyk, O. J. Org. Chem., 2002, 67, 526-532.
68. Van Zijl, P. C., Moonen, C. T. J. Mag. Reson., 1990, 87, 18.
69. Rousselot-Pailley, P., Ede, N. J., Lippens, G. J. Comb. Chem., 2001, 3, 559-563.
70. Rousselot-Pailley, P., Maux, D., Wieruszeski, J.-M., Aubagnac, J.-L., Martinez, J., Lippens G. Tetrahedron, 2000, 56, 5163-5167.
71. Brinkmann, A., Eden, M., Levitt, M. H. J. Chem. Phys., 2000, 112, 8539.
72. Levitt, M. H., Raleigh, D. P., Creuzet, F., Griffin, R. G. J. Chem. Phys., 1990, 92, 6347.
73. Benett, A. E., Rienstra, C. M., Griffiths, J. M., Zhen, W., Lansbury, J., Griffin, P. T., Griffin, R. G. J. Chem. Phys., 1998, 108, 9463.
74. Raya, J., Bianco, A., Furrer, J., Briand, J.-P., Piotto, M., Elbayed, K. J. Mag. Reson., 2002, 157, 43-51.
75. Thieme, K., Zech, G., Kunz, H., Spiess, H. W., Schnell, I. Org. Lett., 2002, 4, 1559-1562.
76. Chin, J., Fell, B., Shapiro, M. J., Tomesch, J., Wareing, J. R., Bray, A. M. J. Org. Chem., 1997, 62, 538-539.
77. Warrass, R., Lippens, G. J. Org. Chem., 2000, 65, 2946-2950.
78. Sarkar, K. S., Garigipati, R. S., Adams, J. L., Keifer, P. A. J. Am. Chem. Soc., 1996, 118, 2305-2306.
79. Pursch, M., Schlotterbeck, G., Tseng, L.-H., Albert, K., Rapp, W. Angew. Chem., 1996, 108, 3034-3036.
80. Riedl, R., Tappe, R., Berkessel, A. J. Am. Chem. Soc., 1998, 120, 8994-9000.
81. Rossé, G., Ouertani, F., Schröder, H. J. Comb. Chem., 1999, 1, 397-401.
82. Shapiro, M. J., Kumaravel, G., Petter, R. C., Beveridge, R. Tetrahedron Lett., 1996, 37, 4671-4674.
83. Guino, M., Brule, E., de Miguel, Y. R. J. Comb. Chem., 2003, 5, 161-165.
84. Gong, Y.-D., Seo, J.-S., Hwang, J. Y.; Park, J. Y., Yoo, S.-E. J. Comb. Chem., 2003, 5, 577-589.
85. Warrass, R., Wieruszeski, J.-M., Boutillon, C., Lippens, G., J. Am. Chem. Soc., 2000, 122, 1789-1795.
86. Hany, R., Rentsch, D., Dhanapal, B., Obrecht, D. J. Comb. Chem., 2001, 3, 85-89.
87. Conde-Friesboes, K., Schjeltved, R. K., Breinholt, J. J. Org. Chem., 2002, 67, 8952-8957.
88. Miguel, de Y. R., Bampos, N., Nalin de Silva, K. M., Richards, S. A., Sanders, J. K. M. Chem. Commun., 1998, 2267-2268.
89. Pellecchia, M., Sem, D. S., Wuethrich, K. Nature Reviews Drug Discovery, 2002, 1, 211-219.
90. Sem, D. S., Pellecchia, M. Curr. Opin. Drug Discov., 2001, 4, 479-492.
91. Keifer, P. A. Curr. Opin. Chem. Biol., 2003, 7, 388-394.