High-resolution NMR techniques for solid-phase synthesis and combinatorial chemistry

Drug Discovery Today

Volumn 2, Issue 11, 1997, Pages 468-478

  Keifer, Paul A ^a  

^a Varian Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DEVELOPMENT; DRUG SYNTHESIS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW;

EID: 0030869479     PISSN: 13596446     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-6446(97)01104-5     Document Type: Review

References (88)

1. Balkenhohl, F. et al. (1996) Angew. Chem., Int. Ed. Engl. 35, 2288-2337
2. Leibfritz, D. et al. (1978) Tetrahedron 34, 2045-2050
3. Blossey, E.C. et al. (1990) J. Org. Chem. 55, 4664-4668
4. Lebl, M. et al. (1995) Biopolymers 37, 177-198
5. Jung, G. and Beck-Sickinger, A.G. (1992) Angew. Chem., Int. Ed. Engl. 31, 367-383
6. Gallop, MA. et al. (1994) J. Med. Chem. 37, 1233-1251
7. Fréchet, J.M.J. (1981) Tetrahedron 37, 663-683
8. Egner, B.J. and Bradley, B. (1997) Drug Discovery Today 2, 102-109
9. Wooten, J.B. (1985) J. Agric. Food. Chem. 33, 419-25
10. Pople, J.A., Schneider, W.G. and Bernstein, H.J. (1959) High-resolution Nuclear Magnetic Resonance, Chapters 4, 5 and 16, McGraw-Hill Book Co.
11. Fyfe, C.A. (1983) Solid State NMR for Chemists, C. F. C. Press
12. Keifer, P.A. et al. (1996) J. Magn. Reson. A 119, 65-75
13. Mazure, M. et al. (1986) C.R. Acad. Sci. (Ser. II) 303, 553-556
14. Auzanneau, F.I., Meldal, M. and Bock, K. (1995) J. Peptide Sci. 1, 31-44
15. Forman, F.W. and Sucholeiki, I. (1995) J. Org. Chem. 60, 523-528
16. MacDonald, A.A. et al. (1995) Mol. Diversity 1, 183-186
17. Look, G.C. et al. (1994) J. Org. Chem. 59, 7588-7590
18. Albericio, F. et al. (1989) J. Org. Chem. 54, 360-366
19. Swerdloff, M.D. et al. (1989) Int. J. Pept. Protein Res. 33, 318-327
20. Ludwick, A.G. et al. (1986) J. Am. Chem. Soc. 108, 6493-6496
21. Giralt, F., Rizo, J. and Pedroso, E. (1984) Tetrahedron 40, 4141-4152
22. Epton, R., Goddard, P. and Ivin, K.J. (1980) Polymer 21, 1367-1371
23. Sternlicht, H. et al. (1971) J. Am. Chem. Soc. 93, 199-208
24. Svensson, A., Fex, T. and Kihlberg. J. (1996) Tetrahedron Lett. 37, 7649-7652
25. Manatt, S.L. et al. (1980) Tetrahedron Lett. 21, 1397-1400
26. Quarrell, R. et al. (1995) Mol. Diversity 1, 223-232
27. Johnson, C.R. and Zhang, B. (1995) Tetrahedron Lett. 36, 9253-9256
28. Bardella, F. et al. (1993) Med. Chem. Lett. 3, 2793-2796
29. Barn, D.R., Morphy, J.R. and Rees, D.C. (1996) Tetrahedron Lett. 37, 3213-3216
30. Holmes, C.P. and Jones, D.G. (1995) J. Org. Chem. 60, 2318-2319
31. Gordeev, M.F., Patel, D.V. and Gordon, E.M. (1996) J. Org. Chem. 61, 924-928
32. Gordeev, M.F. et al. (1996) Tetrahedron Lett. 37, 4643-4646
33. Plunkett, M.J. and Ellman, J.A. (1995) J. Am. Chem. Soc. 117, 3306-3307
34. DeWitt, S.H. et al. (1993) Proc. Natl. Acad. Sci. U. S. A. 90, 6909-6913
35. Nicolaou, K.C. et al. (1997) J. Am. Chem Soc. 119, 449-450
36. Han, H. et al. (1995) Proc Natl. Acad. Sci. U. S. A. 92, 6419-6423
37. Han, H. and Janda, K.D. (1996) J. Am. Chem. Soc. 118, 2539-2544
38. Kim, R.M. (1996) Proc. Natl. Acad. Sci U. S. A. 93, 10012-10017
39. Bayer, E. et al. (1990) Macromolecules 23, 1937-1940
40. Larhed, M., Lindeberg, G. and Hallberg, A. (1996) Tetrahedron Lett. 37, 8219-8222
41. Drain, L.E. (1962) Proc. Phys. Soc. 80, 1380-1382
42. Doskocilová, D. and Schneider, B. (1970) Chem. Phys. Lett. 6, 381-384
43. Doskocilová, D., Schneider, B. and Trekoval, J. (1974) Collect. Czech. Chem. Commun. 39, 2943-2948
44. Doskocilová, D., Schneider, B. and Jakes, J. (1978) J. Magn. Reson. 29. 79-90
45. Ganapathy, S. et al. (1989) Macromolecules 22, 2023-2035
46. Stöver, H.D.H. and Fréchet, J.M J. (1989) Macromolecules 22, 1574-1576
47. Stöver, H.D.H. and Fréchet, J.M J. (1991) Macromolecules 24, 883-888
48. Morgan, K.R. et al. (1994) Carbohydr. Res. 262, 185-194
49. Fitch, W.L. et al. (1994) J. Org. Chem. 59, 7955-7956
50. Keifer, P.A. (1996) J. Org. Chem. 61, 1558-1559
51. Kempe, M., Keifer, P.A. and Barany, G. in Proceedings from the 24th European Peptide Symposium, 8-13 September 1996, Edinburgh, UK, Mayflower Scientific Ltd, Kingwinford, UK (in press)
52. Springer, C.S., Jr (1994) in NMR in Physiology and Biomedicine (Gillies, R.J., ed.), Chapter 5, Academic Press
53. Barbara, T.M. (1994) J. Magn. Reson. A 109. 265-269
54. Chenera, B., Finkelstein, J.A. and Veber, D.F. (1995) J. Am. Chem. Soc. 117, 11999-12000
55. Ruhland, B. et al. (1996) J. Am. Chem. Soc. 118, 253-254
56. Gordon, E.M., Gallop, M.A. and Patel, D.V. (1996) Acc. Chem. Res. 29, 144-154
57. Wehler, T. and Westman, J. (1996) Tetrahedron Lett. 37, 4771-4774
58. Manzi, A. et al. (1995) J. Biol. Chem. 270, 9154-9163
59. Chauret, D.C. et al. (1996) Tetrahedron Lett. 37, 7875-7878
60. Delepierre, M., Prochnicka-Chalufour, A. and Possani, L.D. (1997) Biochemistry 36, 2649-2658
61. Anderson, R.C. et al. (1995) J. Org. Chem. 60, 2650-2651
62. Dhalluin, C. et al. (1996) in Molecular Diversity and Combinatorial Chemistry (Chaiken, I.M. and Janda, K.D., eds), pp. 255-272. American Chemical Society
63. Pursch, M. et al (1996) Angew. Chem., Int. Ed. Engl. 35, 2867-2869
64. Anderson, R.C. et al. (1995) Tetrahedron Lett. 36, 5311-5314
65. Pop, I.E. (1996) Tetrahedron 52, 12209-12222
66. Fuks, L.F. et al. (1992) J. Magn. Reson. 100, 229-242
67. Zelaya, F.O. et al. (1995) J. Magn. Reson. A 115, 131-136
68. Kusama, T. and Hayatsu, H. (1970) Chem. Pharm. Bull. 18, 319-327
69. Merrifield, R.B. (1963) J. Am. Chem. Soc. 85, 2149-2154
70. 1H NMR Spectra of Different SPS Resins with Varying Solvents and Experimental Techniques - An Exploration of Nano•nmr Probe Technology, Varian NMR Instruments
71. Periyasamy, M. and Ford, W.T. (1985) React. Polym. Ion Exch. Sorbents 3, 351-355
72. Sarkar, S.K., Garigipati, R.S., Adams, J.L. and Keifer, P.A. (1996). J. Am. Chem. Soc. 118, 2305-2306
73. Lam, K.S. et al. (1991) Nature 354, 82-84
74. Chabala, J.C. et al. (1994) Perspect. Drug Des. Discovery 2, 305-318
75. Garigipati, R.S. et al. (1996) J. Org. Chem. 61, 2911-2914
76. Ganapathy, S. et al. (1994) Polymers 35, 888-891
77. Maas, W.E., Laukien, F.H. and Cory, D.G. (1996) J. Am. Chem. Soc. 118, 13085-13086
78. Shapiro, M.J. et al. (1996) Tetrahedron Lett. 37, 4671-4674
79. Keifer, P.A. (1996) IBC Symposium Drug Discovery Technology (19-22 August 1996. Boston, MA, USA - poster 11) and Kinki Chemical Society Symposium Combinatorial Chemistry & High Throughput Screening (30-31 January 1997, Osaka Prefecture University, Osaka, Japan)
80. Keifer, P.A. (1996) IBC Symposium Drug Discovery Technology (19-22 August 1996. Boston, MA, USA - poster 11) and Kinki Chemical Society Symposium Combinatorial Chemistry & High Throughput Screening (30-31 January 1997, Osaka Prefecture University, Osaka, Japan)
81. Korhammer, S.A. and Bernreuther, A. (1996) Fresenius J. Anal. Chem. 354, 131-135
82. Sidelmann, U.G. et al. (1995) Anal. Chem. 67, 4441-4445
83. Shockcor, J.P. et al. (1996) Anal. Chem. 68, 4431-4435
84. Wu, N. et al. (1994) J. Am. Chem. Soc. 116, 7929-7930
85. Smallcombe, S.H., Patt, S.L and Keifer, PA. (1995) J. Magn. Reson. A 117, 295-303
86. Patt, S.L. (1991 ) J. Magn. Reson. 95, 94-102
87. Bretthorst, G.L. (1988) Bayesian Spectrum Analysis and Parameter Estimation, Springer Verlag
88. Pullen, F.S. et al. (1995) Rapid Commun. Mass Spectrom. 9, 1003-1006