Solid-phase synthesis of oligoester ion channels

Journal of Organic Chemistry

Volumn 71, Issue 22, 2006, Pages 8545-8551

  Fyles, Thomas M ^a   Hu, Chi Wei ^a   Luong, Horace ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; IONS; PURIFICATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ION CHANNELS; OLIGOESTERS; SOLID-PHASE SYNTHESIS; STRUCTURE-DEPENDENT ACTIVITY;

ESTERS;

CHEMICAL AGENT; ESTER; ION CHANNEL; OLIGOESTER; OLIGOSACCHARIDE; TETRAHYDROPYRAN DERIVATIVE; TETRAHYDROPYRANYL; UNCLASSIFIED DRUG;

ARTICLE; COST; ION TRANSPORT; METHODOLOGY; NONHUMAN; PROCESS OPTIMIZATION; PRODUCTIVITY; PURIFICATION; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION; TRANSPORT VESICLE;

COMBINATORIAL CHEMISTRY TECHNIQUES; ESTERS; FLUORESCENT DYES; ION EXCHANGE; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; UNILAMELLAR LIPOSOMES;

EID: 33750477684     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0615753     Document Type: Article

References (30)

1. For recent reviews on synthetic ion channels: (a) Matile, S.; Som, A.; Sorde, N. Tetrahedron 2004, 60, 6405-6435.
2. (b) Koert, U.; Al-Momani, L.; Pfeifer, J. R. Synthesis 2004, 8, 1129-1146.
3. (c) Koert, U., Ed. Bioorg. Med. Chem. 2004, 12, 1277-1350.
4. Fyles, T. M.; Loock, D.; Zhou, X. J. Am. Chem. Soc. 1998, 120, 2997-3003.
5. Fyles, T. M.; Hu, C. W. J. Supramol. Chem. 2001, 1, 205-215.
6. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
7. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311.
8. Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307-1309.
9. Merrifield, R. B. Angew. Chem. 1985, 97, 801.
10. Franzen, R. G. J. Comb. Chem. 2000, 2, 195-214.
11. For some reviews on solid-phase synthesis: (a) Scott, P. J. H.; Steel, P. G. Eur. J. Org. Chem. 2006, 10, 2251-2268.
12. (b) Ganesan, A. Drug Discovers Today 2002, 7, 47-55.
13. (c) Ganesan, A. Mini-Rev. Med. Chem. 2006, 6, 3-10.
14. (d) Fruechtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
15. (e) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. R. Tetrahedron 1996, 52, 4527-4554.
16. (f) Crowley, J. I.; Rapoport, H. Acc. Chem. Res. 1976, 9, 135-44.
17. Kuisle, O.; Quinoa, E.; Riguera, R. J. Org. Chem. 1999, 64, 8063-8075.
18. Fyles, T. M.; Loock, D.; Zhou, X. Can. J. Chem. 1998, 76, 1015-1026.
19. (a) Alemany, P.; Vilaseca, E. J. Mol. Struct. 1990, 239, 193-203.
20. (b) Galli, C.; Illuminati, G.; Mandolini, L.; Tamborra, P. J. Am. Chem. Soc. 1977, 99, 2591-2597.
21. Meyers, A. I.; Williams, D. R.; White, S.; Erickson, G. W. J. Am. Chem. Soc. 1981, 103, 3088-3093.
22. Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097-3102.
23. For some examples of recent publications using the HPTS dye: (a) Jeon, Y. J.; Kim, H.; Jon, S.; Selvapalam, N.; Oh, D. H.; Seo, I.; Park, C. S.; Jung, S. R.; Koh, D. S.; Kim, K. J. Am. Chem. Soc. 2004, 126, 15944-15945.
24. (b) Madhavan, N.; Robert, E. C.; Gin, M. S. Angew. Chem., Int. Ed. 2005, 44, 7584-7587.
25. (c) Talukdar, P.; Bollot, G.; Mareda, J.; Sakai, N.; Matile, S. Chem.-Eur. J. 2005, 11, 6525-6532.
26. Sidorov, V.; Kotch, F. W.; Abdrakhmanova, G.; Mizani, R.; Fettinger, J. C; Davis, J. T. J. Am. Chem. Soc. 2002, 124, 2267-2278.
27. New, R. R. C. Liposomes: A Practical Approach; IRL Press: Oxford, 1990; pp 105-107.
28. Fyles, T. M.; Knoy, R.; Müllen, K.; Sieffert, M. Langmuir 2001, 17, 6669-6674.
29. Renkes, T.; Schafer, H. J.; Siemens, P. M.; Neumann, E. Angew. Chem., Int. Ed. 2000, 39, 2512-2516.
30. Menger, F. M.; Aikens, P. Angew. Chem., Int. Ed. Engl. 1992, 31, 898-900.