Scope and limitations of solid-supported liquid - Liquid extraction for the high-throughput purification of compound libraries

Journal of Combinatorial Chemistry

Volumn 3, Issue 6, 2001, Pages 528-533

  Breitenbucher, J Guy ^a   Arienti, Kristen L ^a   McClure, Kelly J ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001355923     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc010039f     Document Type: Article

References (31)

1. For reviews see the following. (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815 (a review with 1500 references on solid-supported reagents and scavengers).
2. (b) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41.
3. (c) Weller, H. N. Mol. Diversity 1999, 4, 47.
4. (d) Ferritto, R.; Sensci, P. Drugs Future 1998, 23, 643.
5. (e) An, H. Y.; Cook, P. D. Chem. Rev. 2000, 100, 3311.
6. (a) Boger, D. L.; Ozer, R. S.; Anderson, C. M. Bioorg. Med. Chem. Lett. 1997, 7, 1903.
7. (b) Boger, D. L.; Tarby, C. M.; Myers, P. L.; Caporale, L. H. J. Am. Chem. Soc. 1996, 118, 2109.
8. (c) Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567.
9. (d) Boger, D. L.; Goldberg, J.; Jiang, W. Q.; Chai, W. Y.; Ducray, P.; Lee, J. K.; Ozer, R. S.; Andersson, C. M. Bioorg. Med. Chem. 1998, 6, 1347.
10. (a) Maslana, E.; Schmitt, R.; Pan, J. J. Autom. Methods Manage. Chem. 2000, 22, 187.
11. (b) An exception to these limitations is the "Lollipop Method" developed by Scientists at GlaxoWellcome. Bailey, N.; Cooper, W. J.; Deal, M. J.; Dean, A. W.; Gore, A. L.; Hawes, M. C.; Judd, D. B.; Merritt, A. T.; Storer, R.; Travers, S.; Watson, S. P. Chimica 1997, 51, 832.
12. (c) Rabinowitz, M.; Seneci, P.; Rossi, T.; Dal Cin, M.; Deal, M.; Terstappen, G. Bioorg. Med. Chem. Lett. 2000, 10, 1007.
13. Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. Presented at the 5th International Symposium on Solid Phase Synthesis and Combinatorial Chemical Libraries, London, September 1997. Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097.
14. Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. Presented at the 5th International Symposium on Solid Phase Synthesis and Combinatorial Chemical Libraries, London, September 1997. Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097.
15. (a) Breitenbucher, J. G.; Johnson, C. R.; Haight, M.; Phelan, J. C. Tetrahedron Lett. 1998, 39, 1295.
16. (b) Breitenbucher, J. G.; Hui, H. C. Tetrahedron Lett. 1998, 39, 8207.
17. (c) Breitenbucher, J. G.; Figliozzi, G.; Tetrahedron Lett. 2000, 41, 4311.
18. (d) Yonghan, H.; Baudart, S.; Porco, J. A. J. Org. Chem. 1999, 64, 1049.
19. (e) Peng, S. X.; Henson, C.; Strojnowski, M. J.; Golebiowski, A.; Klopfenstein, S. R. Anal. Chem. 2000, 72, 261.
20. (f) Hone, N. D.; Payne, L. J.; Tice, C. M. Tetrahedron Lett. 2001, 42, 1115.
21. (g) Organ, M. G.; Kaldor, S. W.; Dixon, C. E.; Parks, D. J.; Singh, U.; Lavorato, D. J.; Isbester, P. K.; Siegel, M. G. Tetrahedron Lett. 2000, 41, 8407.
22. (h) Peukert, S.; Jacobsen, E. N. Org. Lett. 1999, 1, 1245.
23. (i) Boldi, A. M.; Dener, J. M.; Hopkins, T. P. J. Comb. Chem. 2001, 3, 367.
24. Personal communications with David C. Jones of Varian Sample Preparation Products.
25. See Extube Applications index at www.varianinc.com/spp/ extapp/html.
26. Peng, S. X.; Branch, T. M.; King, S. L. Anal. Chem. 2001, 73, 708.
27. (a) Gayo, L. M.; Suto, M. J. Tetrahedron Lett. 1997, 38, 513.
28. (b) Lawrence, R. M.; Biller, S. A.; Fryszman, O. M.; Poss, M. A. Synthesis 1997, 553.
29. (c) Warmus, J. S.; da Silva, M. I. Org. Lett. 2000, 2, 1807.
30. Calculated using Chemdraw, version 4.0, Bronto's Fragmentation Method.
31. Products were identified by LC/MS.