Using catalyst-substrate coimmobilization for the discovery of catalysts for asymmetric aldol reactions in split-and-mix libraries

QSAR and Combinatorial Science

Volumn 24, Issue 10, 2005, Pages 1158-1163

  Krattiger, Philipp ^a   Kovàsy, Roman ^a   Revell, Jefferson D ^a   Wennemers, Helma ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Aldol reaction; Asymmetric catalysis; Combinatorial chemistry; Organocatalysis; Peptides; Split and mix libraries

Indexed keywords

BIOCHIPS; CATALYSIS; CATALYSTS; KETONES;

ALDOL REACTIONS; ASYMMETRIC ALDOL REACTIONS; ASYMMETRIC CATALYSIS; COIMMOBILIZATION; COMBINATORIAL CHEMISTRY; ORGANOCATALYSIS; REACTION PARTNERS; SCREENING METHODS; SPLIT-AND-MIX LIBRARY; ]+ CATALYST;

LIBRARIES;

PEPTIDE;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; COMBINATORIAL CHEMISTRY; IMMOBILIZATION; PRIORITY JOURNAL; SCREENING;

EID: 30144432237     PISSN: 1611020X     EISSN: None     Source Type: Journal    
DOI: 10.1002/qsar.200540009     Document Type: Article

References (26)

1. a) M. Hechavarría Fonseca, B. List, Curr. Opin. Chem. Biol. 2004, 8, 319-326.
2. b) M. Meldal, Curr. Opin. Chem. Biol. 2004, 8, 238-244.
3. c) A. Berkessel, Curr. Opin. Chem. Biol. 2003, 7, 409-419.
4. a) A. Furka, F. Sebestyén, M. Asgedom, G. Dibô, Int. J. Pept. Protein Res. 1991, 37, 487-493.
5. b) K. S. Lam, S. E. Salmon, E. M. Hersh, V. J. Hruby, W. M. Kazmierski, R. J. Knapp, Nature 1991, 354, 82-84.
6. S. J. Taylor, J. P. Morken, Science 1998, 280, 267-270.
7. a) G. T. Copeland, S. J. Miller, J. Am. Chem. Soc. 2001, 123, 6496-6502.
8. b) S. J. Miller, Acc. Chem. Res. 2004, 37, 601-610.
9. A. Berkessel, D. A. Hérault, Angew. Chem. 1999, 111, 99-102;
10. Angew. Chem. Int. Ed. 1999, 38, 102-105.
11. a) M. Müller, T. W. Mathers, A. P. Davis, Angew. Chem. 2001 111, 3929-3931;
12. Angew. Chem. Int. Ed. 2001, 40, 3813-3815.
13. b) R. F. Harris, A. J. Nation, G. T. Copeland, S. J. Miller, J. Am. Chem. Soc. 2000, 122, 11270-11271.
14. c) K.-J. Johansson, M. R. M. Andreae, A. Berkessel, A. P. Davis, Tetrahedron Lett. 2005, 46, 3923-3926.
15. P. Krattiger, C. McCarthy, A. Pfaltz, H. Wennemers, Angew. Chem. Int. Ed. 2003, 42, 1722-1724.
16. P. Krattiger, R. Kovasy, J. D. Revell, S. Ivan, H. Wennemers, Org. Lett. 2005, 7, 1101-1103.
17. a) M. H. J. Ohlmeyer, R. N. Swanson, L. W. Dillard, J. C. Reader, G. Asouline, R. Kobayashi, M. H. Wigler, W. C. Still, Proc. Natl. Acad. Sci. USA 1993, 90, 10 922-10 926.
18. b) H. P. Nestler, P. Bartlett, W. C. Still, J. Org. Chem. 1994, 59, 4723-4724.
19. Library 3: AA1 and AA3 = Gly, D-Val, L-Ala, L-Leu, D-Pro, L-Pro, D-Phe, L-Tyr, D-His, L-His, o-Arg, o-Asp, L-Glu, D-Asn, L-Gln; AA2 = Gly, L-Val, D-Ala, D-Leu, D-Pro, L-Pro, L-Phe, D-Tyr, D-His, L-His, L-Arg, L-Asp, D-Glu, L-Asn, D-Gln. Library 5: AA1 and AA3 = Gly, D-Val, L-Ala, D-Pro, L-Pro, D-Phe, L-Tyr, D-Ser, L-Thr, D-Gln, L-Asn, D-Asp, L-Glu, D-His, L-Arg; AA2 = Gly, L-Val, D-Ala, L-Pro, D-Pro, L-Phe, D-Tyr, L-Ser, o-Thr, L-Gln, o-Asn, L-Asp, D-Glu, L-His, D-Arg.
20. a) K. Burgess, A. I. Liaw, N. Y. Wang, J. Med. Chem. 1994, 37, 2985-2987.
21. b) P.-L. Zhao, R. Zambias, J. A. Bolognese, D. Boulton, K. T. Chapman, Proc. Natl. Acad. Sci. USA 1995, 92, 10212-10216.
22. Peptides 1 and 2 catalyze aldol reactions also when DMF or MeOH are used as solvents with only 10% of acetone. However, typically the ee is lower by 10% and the reactions proceed significantly slower.
23. C. Allemann, R. Gordillo, F. R. Clemente, P. H.-C. Chong, K. N. Houk, Acc. Chem. Res. 2004, 37, 558-569.
24. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396.
25. E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, Anal. Biochem. 1970, 34, 595-598.
26. J. Zhang, G. Drugeon, N. L'hermite, Tetrahedron Lett. 2001, 41, 3599-3601.