Sugar-amide surfactant micelles as effective reaction fields for enantioselective hydrolysis of α-amino acid esters

Langmuir

Volumn 20, Issue 20, 2004, Pages 8504-8509

  Kida, Toshiyuki ^a   Kajihara, Keisuke ^a   Isogawa, Kazuhiko ^a   Zhang, Wanbin ^a   Nakatsuji, Yohji ^a   Ikeda, Isao ^a   Akashi, Mitsuru ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; AROMATIC COMPOUNDS; CHEMICAL BONDS; CRITICAL MICELLE CONCENTRATION; ESTERS; HYDROLYSIS; SUGAR (SUCROSE); SURFACE ACTIVE AGENTS; THERMAL EFFECTS;

ALKYL CHAINS; CHAIN LENGTHS; ENANTIOSELECTIVITY; SUGAR-AMIDE SURFACTANTS;

MICELLES;

AMIDE; AMINO ACID; CARBOHYDRATE; ESTER; SURFACTANT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS; KINETICS; METABOLISM; MICELLE; STEREOISOMERISM;

AMIDES; AMINO ACIDS; CARBOHYDRATES; ESTERS; HYDROLYSIS; KINETICS; MICELLES; MOLECULAR STRUCTURE; STEREOISOMERISM; SURFACE-ACTIVE AGENTS;

AMIDES; AMINO ACIDS; ESTERS; HYDROLYSIS; MICELLES; SUGAR; SURFACTANTS;

EID: 5444268750     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la0489662     Document Type: Article

References (44)

1. Cordes, E. H.; Dunlop, R. B. Acc. Chem. Res. 1989, 2, 329.
2. Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systems; Academic Press: New York, 1975; pp 86-193.
3. Tascioglu, S. Tetrahedron 1996, 52, 11113.
4. Lindström, U. M. Chem. Rev. 2002, 102, 2751.
5. Ihara, Y. J. Chem. Soc., Chem. Commun. 1978, 984.
6. Yamada, K.; Shosenji, H.; Ihara, H. Chem. Lett. 1979, 491.
7. Yamada, K.; Shosenji, H.; Ihara, H.; Otsubo, Y. Tetrahedron Lett. 1979, 2529.
8. Ihara, H.; Ono, S.; Shosenji, H.; Yamada, K. J. Org. Chem. 1980, 45, 1623.
9. Ono, S.; Shosenji, H.; Yamada, K. Tetrahedron Lett. 1981, 2391.
10. Ogino, K.; Tomita, I.; Machiya, K.;Tagaki, W. Chem. Lett. 1982, 1875.
11. Ueoka, R.; Moss, R. A.; Swarup, S.; Matsumoto, Y.; Strauss, G.; Murakami, Y. J. Am. Chem. Soc. 1985, 107, 2185.
12. Ueoka, R.; Matsumoto, Y.; Dozono, H.; Yano, Y.; Hirasa, H.; Goto, K.; Kato, Y. Tetrahedron Lett. 1990, 31, 5311.
13. Ueoka, R.; Cho, M.; Matsumoto, Y.; Goto, K.; Kato, Y.; Harada, K.; Sugii, A. Tetrahedron Lett. 1990, 31, 5335.
14. Ihara, Y.; Asakawa, S.; Igata, K.; Matsumoto, Y.; Ueoka, R. J. Chem. Soc., Perkin Trans. 2 1991, 543.
15. Weijnen, J. G. J.; Koudijs, A.; Engbersen, J. F. J. J. Org. Chem. 1992, 57, 7258.
16. Cleij, M. C.; Drenth, W.; Nolte, R. J. M. Recl. Trav. Chim. Pays-Bas 1993, 112, 1.
17. Goto, K.; Okai, J.; Ejima, Y.; Ito, T.; Okai, H.; Ueoka, R. Nippon Kagaku Kaishi 1995, 351.
18. Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769.
19. Bertoncin, F.; Mancin, F.; Scrimin, P.; Tecilla, P.; Tonellato, U. Langmuir 1998, 14, 975.
20. You, J. S.; Yu, X. Q.; Li, X. S.; Yan, Q. S.; Xie, R. G. Tetrahedron: Asymmetry 1998, 9, 1197.
21. You, J. S.; Yu, X. Q.; Liu, K.; Tao, L.; Xiang, Q. X.; Xie, R. G. Tetrahedron: Asymmetry 1999, 10, 243.
22. Grassert, I.; Oehme, G. J. Organomet. Chem. 2001, 621, 158.
23. You, J. S.; Yu, X. Q.; Su, X. Y.; Wang, T.; Xiang, Q. X.; Yang, M.; Xie, R. G. J. Mol. Catal. A: Chem. 2003, 202, 17.
24. Bunton, C. A.; Robinson, L.; Stam, M. F. Tetrahedron Lett. 1971, 121.
25. Brown, J. M.; Bunton, C. A. J. Chem. Soc., Chem. Commun. 1974, 969.
26. Kawaguchi, K.; Isobe, K.; Ohkatsu, Y.; Kusano, T. J. Jpn. Oil Chem. Soc. 1992, 41, 458.
27. Scrimin, P.; Tecilla, P.; Tonellato, U. J. Org. Chem. 1994, 59, 4194.
28. Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 2723.
29. Diego-Castro, M. J.; Hailes, H. C. Chem. Commun. 1998, 1549.
30. Kida, T.; Isogawa, K.; Zhang, W.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4339.
31. Rico-Lattes, I.; Schmitzer, A.; Perez, E.; Lattes, A. Chirality 2001, 13, 24.
32. Nakagawa, T.; Tori, K.; Kuriyama, K. Nihon Kagaku Zasshi 1958, 77, 1684.
33. Perez-Benito, E.; Rodenas, E. J. Colloid Interface Sci. 1990, 139, 87.
34. Bodanszky, M.; Vigneaud, Vdu. J. Am. Chem. Soc. 1959, 81, 5688.
35. Williams, T. J.; Plessas, N. R.; Goldstein, I. J. Carbohydr. Res. 1978, 67, C1.
36. Kobayashi, K.; Sumitomo, H.; Ina, Y. Polym. J. 1985, 17, 567.
37. Moore, S.; Link, K. P. J. Biol. Chem. 1940, 133, 293.
38. Kida, T.; Isogawa, K.; Morishima, N.; Zhang, W.; Masuyama, A.; Nakatsuji, Y.; Ikeda, I. J. Jpn. Oil Chem. Soc. 1998, 47, 41.
39. Briggs, C. B. A.; Newington, I. M.; Pitt, A. R. J. Chem. Soc., Chem. Commun. 1995, 379.
40. Rosen, M. J. Surfactants and Interfacial Phenomena, 2nd ed.; John Wiley & Sons: New York, 1989; pp 129-130.
41. Böcker, Th.; Münster, J. T. Tenside, Surfactants, Deterg. 1889, 26, 318.
42. Aveyard, R.; Binks, B. P.; Chen, J.; Esquena, J.; Fletcher, P. D. I. Langmuir 1998, 14, 4699.
43. Schmidt, R. R.; Jankowski, K. Liebigs Ann. 1996, 867.
44. Rosen, M. J. Surfactants and Interfacial Phenomena, 2nd ed.; John Wiley & Sons: New York, 1989; pp 114-118.