A class II aldolase mimic

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 4845-4853

  Hedin Dahlström, Jimmy ^a   Rosengren Holmberg, Jenny P ^a   Legrand, Sacha ^a   Wikman, Susanne ^a   Nicholls, Ian A ^a  

^a LINNAEUS UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; DIBENZOYLMETHANE; ENANTIOSELECTIVE RECOGNITION; IMPRINTED POLYMERS;

ALDEHYDES; BENZENE; CARBON CARBON COMPOSITES; CHEMICAL BONDS; CHEMICAL REACTIONS; COPOLYMERS; MONOMERS; NUCLEAR MAGNETIC RESONANCE; POLYMERS; SUBSTRATES; TITRATION;

ENZYMES;

3 BENZOYL 1,7,7 TRIMETHYLBICYCLO[2.2.2]HEPTAN 2 ONE; 4 VINYLPYRIDINE; BENZALDEHYDE; CAMPHOR; COBALT COMPLEX; COPOLYMER; DIBENZOYLMETHANE DERIVATIVE; DIVINYLBENZENE; FRUCTOSE BISPHOSPHATE ALDOLASE; KETONE; MONOMER; POLYMER; STYRENE; SYNTHETIC POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; COMPETITIVE INHIBITION; COVALENT BOND; ENANTIOSELECTIVITY; MOLECULAR IMPRINTING; MOLECULAR INTERACTION; MOLECULAR MIMICRY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SPECTROSCOPY; TITRIMETRY;

ALDEHYDE-LYASES; BENZALDEHYDES; CAMPHOR; CATALYSIS; CHALCONES; COBALT; KETONES; KINETICS; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POLYMERS; STEREOISOMERISM; TIME FACTORS;

EID: 33745441577     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060608b     Document Type: Article

References (76)

1. (a) Danishefsky, S. Science 1993, 259, 469-470.
2. (b) Sukumaran, J.; Hanefeld, U. Chem. Soc. Rev. 2005, 34, 530-42.
3. (a) Bornscheuer, U. T.; Kazlauskas, R. J. Angew. Chem., Int. Ed. 2004, 43, 6032-6040.
4. (b) Jaeger, K.-E.; Eggert, T. Curr. Opin. Biotechnol. 2004, 15, 305-313.
5. (a) Lilley, D. M. J. Curr. Opin. Struct. Biol. 2005, 15, 313-323.
6. (b) Sigel, R. K. O. Eur. J. Inorg. Chem. 2005, 12, 2281-2292.
7. Severin, K. Curr. Opin. Chem. Biol. 2000, 4, 710-714.
8. Mastrorilli, P.; Nobile, C. F. Coord. Chem. Rev. 2004, 248, 377-395.
9. Schultz, P. G.; Yin, J.; Lerner, R. A. Angew. Chem., Int. Ed. 2002, 41, 4427-4437.
10. Alexander, C.; Davidson, L.; Hayes, W. Tetrahedron 2003, 59, 2025-2057.
11. (a) Sellergren, B., Ed. Molecularly Imprinted Polymers. Man-made Mimics of Antibodies and Their Applications in Analytical Chemistry, Elsevier: Amsterdam, The Netherlands, 2001.
12. (b) Yan, M.; Ramström, O., Eds. Molecularly Imprinted Materials. Science and Technology; Marcel Dekker: New York, 2005.
13. (c) Alexander, C.; Andersson, H. S.; Andersson, L. I.; Ansell, R. J.; Kirsch, N.; Nicholls, I. A.; O'Mahony, J.; Whitcombe, M. J. J. Mol. Recognit. 2006, 19, 106-180.
14. (a) Whitcombe, M. J.; Alexander, C.; Vulfson, E. N. Synlett 2000, 6, 911-923.
15. (b) Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686.
16. (c) Bruggemann, O. Anal. Chim. Acta 2001, 435, 197-207.
17. (d) Tada, M.; Iwasawa, Y. J. Mol. Catal. A 2003, 199, 115-137.
18. (e) Toorisaka, E.; Uezu, K.; Goto, M.; Furusaki, S. Biochem., Eng. J. 2003, 14, 85-91.
19. (f) Striegler, S. J. Chromatogr. B 2004, 804, 183-195.
20. (g) Cheng, Z. Y.; Zhang, L. W.; Li, Y. Z. Chem. Eur. J. 2004, 10, 3555-3561.
21. Svenson, J.; Nicholls, I. A. Anal. Chim. Acta 2001, 435, 19-24.
22. (a) Strikovsky, A. G.; Kasper, D.; Grün, M.; Green, B. S.; Hradil, J.; Wulff, G. J. Am. Chem. Soc. 2000, 122, 6295-6296.
23. (b) Wulff, G.; Gross, T.; Schönfeld, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1961-1964.
24. (c) Sellergren, B.; Shea, K. J. Tetrahedron: Asymmetry 1994, 5, 1403-1406.
25. (d) Sellergren, B.; Karmalkar, R. N.; Shea, K. J. J. Org. Chem. 2000, 65, 4009-4027.
26. Svenson, J.; Zheng, N.; Nicholls, I. A. J. Am. Chem. Soc. 2004, 126, 8554-8560.
27. (a) Müller, R.; Andersson, L. I.; Mosbach, K. Makromol. Chem.-Rapid Commun. 1993, 14, 637-641.
28. (b) Beach, J. V.; Shea, K. J. J. Am. Chem. Soc. 1994, 116, 379-380.
29. Matsui, J.; Nicholls, I. A.; Karube, I.; Mosbach, K. J. Org. Chem. 1996, 61, 5414-5417.
30. (a) Liu, X.-C.; Mosbach, K. Macromol. Rapid Commun. 1997, 18, 609-615.
31. (b) Visnjevski, A.; Schomäcker, R.; Yilmaz, E.; Brüggemann, O. Catal Commun. 2005, 6, 601-606.
32. (c) Busi, E.; Basosi, R.; Ponticelli, F.; Olivucci, M. J. Mol. Catal. A: Chem. 2004, 217, 31-36.
33. Cammidge, A. N.; Baines, N. J.; Bellingham, R. K. Chem. Commun. 2001, 2588-2589.
34. Mikami, K.; Yajima, T.; Takasaki, T.; Matsukawa, S.; Terada, M.; Uchimaru, T.; Maruta, M. Tetrahedron 1996, 52, 85-98.
35. Mahrwald, R., Ed. Modern Aldol Reactions, Vol. I: Enolates, Organocatalysis, Biocatalysis and Natural Product Synthesis; Wiley-VCH Verlag GmbH & Co., KGaA: Weinheim, Germany, 2004.
36. Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352-1374.
37. Mahrwald, R., Ed. Modern Aldol Reactions, Vol. 2: Metal Catalysis; Wiley-VCH Verlag GmbH & Co., KGaA: Weinheim, Germany, 2004.
38. (a) Evans, D. A.; Kim, A. S. In Handbook of Reagents for Organic Synthesis: Reagents, Auxiliaries and Catalysts for C-C Bonds; Coates, R. M., Denmark, S. E., Eds.; John Wiley & Sons: New York, 1999; pp 91-101.
39. (b) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
40. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-115.
41. (a) Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 1998, 120, 2768-2779.
42. (b) Zhong, G.; Lerner, R. A.; Barbas, C. F., III Angew. Chem., Int. Ed. 1999, 38, 3738-3741.
43. (a) Calter, M. A.; Song, W.; Zhou, J. G. J. Org. Chem, 2004, 69, 1270-1275.
44. (b) Saito, S.; Yamamoto, H. Acc. Chem. Res. 2004, 37, 570-579.
45. Heron, E. J.; Caprioli, R. M. Biochim. Biophys. Acta 1975, 403, 563-572.
46. Tiecco, M.; Testaferri, L.; Marini, F.; Sternativo, S.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahedron: Asymmetry 2004, 15, 783-791.
47. Knollmuller, M.; Ferencic, M.; Gärtner, P.; Mereiter, K.; Noe, C. R. Tetrahedron: Asymmetry 1998, 9, 4009-4020.
48. Palomo, C.; Oiarbide, M.; Aizpurua, J. M.; González, A.; García, J. M.; Landa, C.; Odriozola, I.; Linden, A. J. Org. Chem. 1999, 64, 8193-8200.
49. Palomo, C.; Oiarbide, M.; Mielgo, A.; González, A.; García, J. M.; Landa, C.; Lecumberri, A.; Linden, A. Org. Lett. 2001, 3, 3249-3252.
50. (a) Gupta, S. N.; Neckers, D. C. J. Polym. Sci., Polym. Chem. Ed. 1982, 20, 1609-1622.
51. (b) Vidyasankar, S.; Ru, M.; Arnold, F. H. J. Chromatogr. A 1997, 775, 51-63.
52. (c) Hart, B. R.; Shea, K. J. J. Am. Chem. Soc. 2001, 123, 2072-2073.
53. (d) Takeuchi, T.; Mukawa, T.; Matsui, J.; Higashi, M.; Shimizu, K. D. Anal. Chem. 2001, 73, 3869-3874.
54. (e) Efendiev, A. A. Macromol. Symp. 1994, 80, 289-313.
55. (f) Matsui, J.; Nicholls, I. A.; Takeuchi, T.; Mosbach, K.; Karube, I. Anal. Chim. Acta 1996, 335, 71-77.
56. (g) Fujii, Y.; Matsutani, K.; Kikuchi, K. J. Chem. Soc., Chem. Commun. 1985, 415-417.
57. (h) Dhal, P. K.; Arnold, F. H. J. Am. Chem. Soc. 1991, 113, 7417-7418.
58. (i) Striegler, S.; Tewes, E. Eur. J. Inorg. Chem. 2002, 487-495.
59. (j) Striegler, S. Anal. Chim. Acta 2005, 539, 91-95.
60. (k) Striegler, S.; Dittel M. Anal. Chim. Acta 2003, 484, 53-62.
61. (a) Brunkan, N. M.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 6217-6225.
62. (b) Santora, B. P.; Larsen, A. O.; Gagné, M. R. Organometallics 1998, 17, 3138-3140.
63. (c) Koh, J. H.; Larsen, A. O.; White, P. S.; Gagné, M. R. Organometallics 2002, 21, 7-9.
64. (d) Wulff, G.; Vietmeier, J. Makromol. Chem. - Macromol. Chem Phys. 1989, 190, 1727-1735.
65. (e) Leonhardt, A.; Mosbach, K. React. Polym. 1987, 6, 285-290.
66. Togni, A. Organometallics 1990, 9, 3106-3113.
67. Wei, H.-X.; Wang, Z.-M.; Shi, M. Chem. Pharm. Bull. 1999, 47, 909-910.
68. Namy, J. L.; Girard, P.; Kagan, H. B. Nouv. J. Chim. 1977, 1, 5-7.
69. Chuiko, V. A.; Vinarskaya, Z. V.; Izotova, L. V.; Tychinskaya, L. Y. Russ. J. Org. Chem. 2002, 38, 196-199.
70. (a) Kim, H.; Spivak, D. A. J. Am. Chem. Soc. 2003, 125, 11269-11275.
71. (b) Takeuchi, T.; Dobashi, A.; Kimura, K. Anal. Chem. 2000, 72, 2418-2422.
72. (c) Striegler, S. Bioseparation 2001, 10, 307-314.
73. (d) Wulff, G.; Knorr, K. Bioseparation 2001, 10, 257-276.
74. Karlsson, J. G.; Andersson, L. I.; Nicholls, I. A. Anal. Chim. Acta 2001, 435, 57-64.
75. Adbo, K.; Nicholls, I. A. Anal. Chim. Acta 2001, 435, 115-120.
76. Watanabe, K.; Imazawa, A. Bull. Chem. Soc. Jpn. 1982, 55, 3208-3211.