Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2370-2380

  Holmes, Christopher P ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001125895     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961602x     Document Type: Article

References (54)

1. Combinatorial chemistry reviews: (a) Terrett, N. K., Gardner, M., Gordon, D. W., Kobylecki, R. J., Steele, J. Tetrahedron 1995, 51, 8135-8173. (b) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
2. Combinatorial chemistry reviews: (a) Terrett, N. K., Gardner, M., Gordon, D. W., Kobylecki, R. J., Steele, J. Tetrahedron 1995, 51, 8135-8173. (b) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
3. Combinatorial chemistry reviews: (a) Terrett, N. K., Gardner, M., Gordon, D. W., Kobylecki, R. J., Steele, J. Tetrahedron 1995, 51, 8135-8173. (b) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
4. Solid phase organic synthesis reviews: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (b) Früchtel, J. S.; Jung, G. Angew. Chem. 1996, 35, 17-41. Patel, D. V.; Gordon, E. M. Drug Disc. Today 1996, 4, 134-144.
5. Solid phase organic synthesis reviews: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (b) Früchtel, J. S.; Jung, G. Angew. Chem. 1996, 35, 17-41. Patel, D. V.; Gordon, E. M. Drug Disc. Today 1996, 4, 134-144.
6. Solid phase organic synthesis reviews: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (b) Früchtel, J. S.; Jung, G. Angew. Chem. 1996, 35, 17-41. Patel, D. V.; Gordon, E. M. Drug Disc. Today 1996, 4, 134-144.
7. For a general review of the use of photolabile supports see: Lloyd- Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065-11133. For the general use of photoprotecting groups see: Pallai, V. N. R. Synthesis 1980, 1-26.
8. For a general review of the use of photolabile supports see: Lloyd- Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065-11133. For the general use of photoprotecting groups see: Pallai, V. N. R. Synthesis 1980, 1-26.
9. Rich, D. H.; Gurwara, S. K. J. Chem. Soc., Chem. Commun. 1973, 610-611.
10. (a) Rich, D. H.; Gurwara, S. K. J. Am. Chem. Soc. 1975, 97, 1575-1579.
11. (b) Rich, D. H.; Gurwara, S. K. Tetrahedron Lett. 1975, 301-304.
12. (c) Hammer, R. P.; Albericio, F.; Gera, L.; Barany, G. Int. J. Pept. Protein Res. 1990, 36, 31-45.
13. Lloyd-Williams, P.; Albericio, F.; Giralt, E. Int. J. Pept. Protein Res. 1991, 37, 58-60.
14. (e) Lloyd-Williams, P.; Gairí, M; Albericio, F.; Giralt, E Tetrahedron 1993, 49, 10069-10078.
15. (f) Giralt, E.; Albericio, F.; Dalcol, L; Gairí, M.; Lloyd-Williams, P.; Rabanal, F. In Innovation and Perspectives in Solid Phase Synthesis; Epton, R., Ed.; Mayflower Worldwide Ltd.: Birmingham, UK, 1994; pp 51-60.
16. (a) Burbaum, J. J.; Ohlmeyer, M. H. J.; Reader, J. C.; Henderson, I.; Dillard, L. W.; Li, G.; Randle, T. L.; Sigal, N. H.; Chelsjy, D.; Baldwin, J. J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6027-6031.
17. Ohlmeyer, M. H. J.; Swanson, R. N.; Dillard, L. W.; Reader, J. C.; Asouline, G.; Kobayashi, R.; Wigler, M.; Still, W. C. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 10922-10926.
18. Wang, S. W. J. Org. Chem. 1976, 41, 3258-3261.
19. (a) Tjoeng, F. S.; Heavner, G. A. J. Org. Chem. 1983, 48, 355-359.
20. (b) Bellof, D.; Mutter, M. Chimia 1985, 39, 317-320.
21. The undesired oxidation most likely stems from the prolonged exposure to UV light and not from interaction of the products with the resin-bound photolysis byproducts. Workers have noted that photolysis of methionine in solution for 16 h in the absence of an o-nitrobenzyl linker resulted in a 1:1 mixture of methionine:methionine sulfoxide; see ref 5c.
22. (a) Patchnornik, A.; Amit, B.; Woodward, R. B. J. Am. Chem. Soc. 1970, 92, 6333-6335.
23. (b) Reid, W.; Wilk, M. Justus Liebigs Ann. Chem. 1954, 590, 91.
24. Tjoeng, F. S.; Tam, J. P.; Merrifield, R. B. Int. J. Pept. Protein Res. 1979, 14, 262-274.
25. Ajayaghosh, A; Pillai, R. Tetrahedron 1988, 44, 6661-6666.
26. Ajayaghosh, A.; Pillai, V. N. R. J. Org. Chem. 1987, 52, 5714-5717.
27. Ajayaghosh, A.; Pillai, V. N. R. Tetrahedron Lett. 1995, 36, 777-780.
28. Brown, B. B.; Wagner, D. S.; Geysen, H. M. Mol. Diversity 1995, 1, 4-12.
29. (a) McMinn, D. L.; Greenberg, M. M. Tetrahedron 1996, 52, 3827-3840.
30. (b) Venkatesan, H.; Greenberg, M. M. J. Org. Chem. 1996, 61, 525-529.
31. (c) Yoo, D. J.; Greenberg, M. M. J. Org. Chem. 1995, 60, 3358-3364.
32. Greenberg, M. M.; Gilmore, J. L. J. Org. Chem. 1994, 59, 746-753 .
33. Rock, R. S.; Chan, S. I. J. Org. Chem. 1996, 61, 1526-152 9.
34. (a) Holmes, C. P.; Jones, D. G. J. Org. Chem. 1995, 60, 2318-2319.
35. (b) Holmes, C. P.; Jones, D. G.; Frederick, B. T.; Dong, L.-C. In Peptides: Chemistry, Structure and Biology (Proceedings of the 14th American Peptide Symposium); Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd: Birmingham, 1995; pp 44-45.
36. The molecules lead to the nitrosoacetophenone; the characterization and subsequent reactivity of the nitrosoacetophenone photoproduct will be reported in due course.
37. (a) Holmes, C. P.; Chinn, J. P.; Look, G. C.; Gordon, E. M.; Gallop, M. A. J. Org. Chem. 1995, 60, 7328-7333.
38. (b) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253-254.
39. Alternatively referred to as "handles".
40. Since photolytic cleavage is first order with respect to UV light intensity, it is the combination of lamp intensity and photolysis time (in addition to wavelength) which should be reported to quantify the amount of light delivered.
41. Barany, G.; Albericio, F. J. Am. Chem. Soc. 1985, 107, 4936-4942.
42. Dermer, O. C.; King, J. J. Org. Chem. 1943, 8, 168-173.
43. Drefahl, G.; Fisher, F. Justus Liebigs Ann. Chem. 1956, 598, 159.
44. The heightened susceptibility toward acidic cleavage as one increases the chain length of the anchoring tail is well known; see for example ref 2 and Albericio, F.; Barany, G. Int. J. Pept. Protein Res. 1990, 30, 206-216.
45. (a) Holmes, C. P.; Adams, C. L.; Kochersperger, L. M.; Mortensen, R. B.; Aldwin, L. A. Biopolymers 1995, 37, 199-211.
46. (b) Pease, A. C.; Solas, D.; Sullivan, E. J.; Cronan, M. T.; Holmes, C. P.; Fodor, S. P. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 5022-5026.
47. (c) Pirrung, M. C.; Bradley, J.-C. J. Org. Chem. 1995, 60, 116-117.
48. 2.
49. Walker, J. W.; Reid, G. P.; McCray, J. A.; Trentham, D. R. J. Am. Chem. Soc. 1988, 110, 7170-7177.
50. Ramesh, D.; Wieboldt, R.; Billington, A. P.; Carpenter, B. K.; Hess, G. P. J. Org. Chem. 1993, 58, 4599-5605.
51. Other workers have reported poor yields for the reductive amination of 2-nitro-4,5-dimethoxyacetophenone: Wilcox, M.; Viola, R. W.; Johnson, K. W.; Billington, A. P.; Carpenter, B. K.; McCray, J. A.; Guzikowski, A. P.; Hess, G. P. J. Org Chem. 1990, 55, 1585-1589.
52. Baer, T. A.; Raillard, S. P. Unpublished results.
53. Look, G. C.; Holmes, C. P.; Chinn, J. P.; Gallop, M. A. J. Org. Chem. 1994, 59, 7588-7590.
54. A polyethyleneglycol - polystyrene based support (TentaGel) was used.