Towards peptide isostere libraries: Aqueous aldol reactions on hydrophilic solid supports

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 6, 2000, Pages 955-962

  Graven, Anette ^a   Grotli, Morten ^a   Meldal, Morten ^a  

^a CARLSBERG LABORATORY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; DERIVATIVES; GRAFTING (CHEMICAL); HYDROPHILICITY; MONOMERS; OPTIMIZATION; POLYETHYLENE GLYCOLS; RESINS; SOLVENTS;

AQUEOUS ALDOL REACTIONS;

CHEMICAL REACTIONS;

EID: 0034696478     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909246c     Document Type: Article

References (52)

1. Combinatorial Peptide and Non-Peptide Libraries: A Handbook, ed. G. Jong, VCH, Weinheim, New York, Basel, Cambridge, Tokyo, 1996.
2. A. F. Spatola, in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, ed. B. Weinstein, Marcel Dekker, New York, 1983.
3. D. H. Rich, in Comprehensive Medicinal Chemistry, ed. C. Mansch, P. G. Sammes and J. B. Tailor, Pergamon Press, Oxford, 1989.
4. M. A. Gallop, R.'-W. Barret, W. J. Dower, S. P. A. Fodor and E. M. Gordon, J. Med. Chem., 1994, 37, 1233.
5. E. M. Gordon, R. W. Barret, W. J. Dower, S. P. A. Fodor and M. A. Gallop, J. Med. Chem., 1994, 37, 1385.
6. D. C. Horwell, Bioorg. Med. Chem., 1996, 4, 1573.
7. J. P. Vacca and J. H. Condra, Drug Discovery, 1997, 2, 261.
8. C. H. Heathcock, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon Press, New York, 1991.
9. B. M. Kim, S. F. Williams and S. Masamune, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon Press, New York, 1991.
10. I. Paterson, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon Press, New York, 1991.
11. C. C. Leznoff and J. Y. Wong, Can. J. Chem., 1973, 51, 3756.
12. M. J. Kurth, L. A. A. Randall, C. Chen, C. Melander, R. B. Miller, K. McAllister, G. Reitz, R. Kang, T. Nakatsu and C. Green, J. Org. Chem., 1994, 59, 5862.
13. M. Reggelin and V. Brenig, Tetrahedron Lett., 1996, 37, 6851.
14. S. Kobayashi, I. Hachiya and M. Yasuda, Tetrahedron Lett., 1996, 37, 5569.
15. A; V. Purandare and S. Natarajan, Tetrahedron Lett., 1997, 38, 8777.
16. S. Kobayashi, T. Wakabayshi and M. Yasuda, J. Org. Chem., 1998, 63, 4868.
17. C. W. Phoon and C. Abell, Tetrahedron Lett., 1998, 39, 2655.
18. C. Gennari, S. Ceccarelli, U. Piarulli, K. Aboutayab, M. Donghi and I. Paterson, Tetrahedron, 1998, 54, 14999.
19. T. Mukaiyama, K. Banno and K. Narasaka, J. Am. Chem. Soc., 1974, 96, 7503.
20. R. Noyori, K. Yokoyama, J. Sakata, I. Kuwajima, E. Nakamura and M. Shimizu, J. Am. Chem. Soc., 1977, 99, 1265.
21. S. Murata, M. Suzuki and R. Noyori, J. Am. Chem. Soc, 1980, 102, 3248.
22. S. E. Denmark, B. D. Griedel, D. M. Coe and M. E. Schnute, J. Am. Chem. Soc., 1994, 116, 7026.
23. S. G. Nelson, Tetrahedron: Asymmetry, 1998, 9, 357.
24. H. Groger, E. M. Yogi and M. Shibasaki, Chem. Eur. J., 1998, 4, 1137.
25. S. Saito and H. Yamamoto, Chem. Eur. J., 1999, 5, 1959.
26. N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai and M. Shibasaki, J. Am. Chem. Soc., 1999, 121, 4168.
27. S. Kobayashi and I. Hachiya, J. Org. Chem., 1994, 59, 3590.
28. S. Kobayashi, Synlett, 1994, 689.
29. C. Le Roux, L. Ciliberti, H. Laurant-Robert, A. Laporterie and J. Dubac, SVH/C, 1998, 1249.
30. M. Meldal, Tetrahedron Lett., 1992, 33, 3077.
31. F.-I. Auzanneau, M. Meldal and K. Bock, J. Pept. Sci., 1995, 1, 31.
32. M. Renil and M. Meldal, Tetrahedron Lett., 1996, 37, 6185.
33. A. Schleyer, M. Meldal, M. Renil, H. Paulsen and K. Bock, Angew. Chem., Int. Ed. Engl., 1997, 36, 1976.
34. J. Rademann, M. Meldal and K. Bock, Chem. Eur. J., 1999, 5, 1218.
35. J. Rademann, M. Grotli, M. Meldal and K. Bock, J. Am. Chem. Soc., 1999, 121, 5459.
36. O. Mitsunobu, Synthesis, 1981, 1.
37. B. C. Hamper, D. R. Dukesherer and M. S. South, Tetrahedron Lett., 1996, 37, 3671.
38. V. Krchnak, Z. Flegelova, A. S. Weichsel and M. Lebl, Tetrahedron Lett., 1995, 36, 6193.
39. F. Wang and J. R. Hauske, Tetrahedron Lett., 1997, 38, 6529.
40. R. Devraj and M. Cushman, J. Org. Chem., 1996, 61, 9368.
41. T. A. Rano and K. T. Chapman, Tetrahedron Lett., 1995, 36, 3789.
42. L. S. Richter and T. R. Gadek, Tetrahedron Lett., 1994, 35, 4705.
43. S. Sarshar, D. Siev and A. M. M. Mjalli, Tetrahedron Lett., 1996, 37, 835.
44. J. L. Castro, V. G. Matassa and R. G. Ball, J. Org. Chem., 1994, 59, 2289.
45. E. E. Swayze, Tetrahedron Lett., 1997, 38, 8465.
46. E. E. Swayze, Tetrahedron Lett., 1997, 38, 8643.
47. M. R. Pavia, M. P. Cohen, G. J. Dilley, G. R. Dubuc, T. L. Durgin, F. W. Forman, M. E. Hediger, G. Milot, T. S. Powers, I. Sucholeiki, S. Zhou and D. G. Hangauer, Bioorg. Med. Chem., 1996, 4, 659.
48. E. Hasegawa, K. Ishiyama, T. Horaguchi and T. Shimizu, J. Org. Chem., 1991, 56, 1631.
49. N. Giuseppone, P. Van de Weghe, M. Mellah and J. Collin, Tetrahedron, 1998, 54, 13129.
50. R. Lin, Y. Yu and Y. Zhang, Syntlt. Commun., 1993, 23, 271.
51. K. Hantawong and W. S. Murphy, J. Chem. Res. (M), 1988, 10, 2520.
52. E. Kaiser, Anal. Biochem., 1970, 34, 595.