Remarkable supramolecular catalysis of glycoside hydrolysis by a cyclodextrin cyanohydrin

Journal of the American Chemical Society

Volumn 127, Issue 10, 2005, Pages 3238-3239

  Ortega Caballero, Fernando ^a   Rousseau, Cyril ^a   Christensen, Brian ^a   Petersen, Torben Ellebæk ^a   Bols, Mikael ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENYL BETA D GLUCOSIDE; ALDEHYDE DERIVATIVE; BETA CYCLODEXTRIN DERIVATIVE; CYANOHYDRIN; CYCLODEXTRIN DERIVATIVE; GLUCOSIDE; GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; HYDROGENOLYSIS; HYDROLYSIS; SYNTHESIS;

BIOMIMETIC MATERIALS; CATALYSIS; CYCLODEXTRINS; GLYCOSIDE HYDROLASES; GLYCOSIDES; HYDROLYSIS; KINETICS; NITRILES;

EID: 14944371145     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042678a     Document Type: Article

References (20)

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8. For research on enzyme mimics, see: (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011. (b) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 551-553. (c) Murakami, Y.; Kikuchi, J. I.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (d) Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686. (e) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153. (f) Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605. (g) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1992, 114, 5882-5883. (h) Akiike, T.; Nagano, Y.; Yamamoto, Y.; Nakamura, A.; Ikeda, H.; Veno, A.; Toda, F. Chem. Lett. 1994, 1089-1092. (i) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894. (j) Milovic, N. M.; Badjic, J. D.; Kostic, N. M. J. Am. Chem. Soc. 2004, 126, 696-697. For previous work on glycosidase mimics, see: (k) Doug, T. H.; Chou, J. Z.; Huang, X.; Bennet, A. J. J. Chem. Soc., Perkin Trans. 2 2001, 83-89.
9. For research on enzyme mimics, see: (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011. (b) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 551-553. (c) Murakami, Y.; Kikuchi, J. I.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (d) Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686. (e) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153. (f) Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605. (g) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1992, 114, 5882-5883. (h) Akiike, T.; Nagano, Y.; Yamamoto, Y.; Nakamura, A.; Ikeda, H.; Veno, A.; Toda, F. Chem. Lett. 1994, 1089-1092. (i) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894. (j) Milovic, N. M.; Badjic, J. D.; Kostic, N. M. J. Am. Chem. Soc. 2004, 126, 696-697. For previous work on glycosidase mimics, see: (k) Doug, T. H.; Chou, J. Z.; Huang, X.; Bennet, A. J. J. Chem. Soc., Perkin Trans. 2 2001, 83-89.
10. For research on enzyme mimics, see: (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011. (b) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 551-553. (c) Murakami, Y.; Kikuchi, J. I.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (d) Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686. (e) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153. (f) Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605. (g) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1992, 114, 5882-5883. (h) Akiike, T.; Nagano, Y.; Yamamoto, Y.; Nakamura, A.; Ikeda, H.; Veno, A.; Toda, F. Chem. Lett. 1994, 1089-1092. (i) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894. (j) Milovic, N. M.; Badjic, J. D.; Kostic, N. M. J. Am. Chem. Soc. 2004, 126, 696-697. For previous work on glycosidase mimics, see: (k) Doug, T. H.; Chou, J. Z.; Huang, X.; Bennet, A. J. J. Chem. Soc., Perkin Trans. 2 2001, 83-89.
11. For research on enzyme mimics, see: (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011. (b) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 551-553. (c) Murakami, Y.; Kikuchi, J. I.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (d) Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686. (e) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153. (f) Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605. (g) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1992, 114, 5882-5883. (h) Akiike, T.; Nagano, Y.; Yamamoto, Y.; Nakamura, A.; Ikeda, H.; Veno, A.; Toda, F. Chem. Lett. 1994, 1089-1092. (i) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894. (j) Milovic, N. M.; Badjic, J. D.; Kostic, N. M. J. Am. Chem. Soc. 2004, 126, 696-697. For previous work on glycosidase mimics, see: (k) Doug, T. H.; Chou, J. Z.; Huang, X.; Bennet, A. J. J. Chem. Soc., Perkin Trans. 2 2001, 83-89.
12. For research on enzyme mimics, see: (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011. (b) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 551-553. (c) Murakami, Y.; Kikuchi, J. I.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (d) Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686. (e) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153. (f) Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605. (g) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1992, 114, 5882-5883. (h) Akiike, T.; Nagano, Y.; Yamamoto, Y.; Nakamura, A.; Ikeda, H.; Veno, A.; Toda, F. Chem. Lett. 1994, 1089-1092. (i) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894. (j) Milovic, N. M.; Badjic, J. D.; Kostic, N. M. J. Am. Chem. Soc. 2004, 126, 696-697. For previous work on glycosidase mimics, see: (k) Doug, T. H.; Chou, J. Z.; Huang, X.; Bennet, A. J. J. Chem. Soc., Perkin Trans. 2 2001, 83-89.
13. For research on enzyme mimics, see: (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011. (b) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 551-553. (c) Murakami, Y.; Kikuchi, J. I.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (d) Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686. (e) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153. (f) Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605. (g) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1992, 114, 5882-5883. (h) Akiike, T.; Nagano, Y.; Yamamoto, Y.; Nakamura, A.; Ikeda, H.; Veno, A.; Toda, F. Chem. Lett. 1994, 1089-1092. (i) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894. (j) Milovic, N. M.; Badjic, J. D.; Kostic, N. M. J. Am. Chem. Soc. 2004, 126, 696-697. For previous work on glycosidase mimics, see: (k) Doug, T. H.; Chou, J. Z.; Huang, X.; Bennet, A. J. J. Chem. Soc., Perkin Trans. 2 2001, 83-89.
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18. s is the substrate dissociation constant), which is the case here. Then d[ES]/dt ≈ 0 is also fulfilled (steady-state conditions) over shorter time periods.
19. s), and the found value (15 mM) is close to the reported dissociation constant of 28 mM for this substrate to β-cyclodextrin.
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