Crown ether activation of cross-linked subtilisin Carlsberg crystals in organic solvents

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1998, Pages 3341-3343

  Van Unen, Dirk Jan ^a   Sakodinskaya, Inna K ^a   Engbersen, Johan F J ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

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[No Author keywords available]

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EID: 33748497829     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Enzymatic reactions in organic media, eds. A. M. P. Koskinen and A. M. Klibanov, Blackie academic & professional, Glasgow, 1996.
2. J. S. Dordick, Enzyme Microb. Technol., 1989, 11, 194.
3. (a) D. N. Reinhoudt, A. M. Eendebak, W. F. Nijenhuis, W. Verboom, M. Kloosterman and H. E. Schoemaker, J. Chem. Soc., Chem. Commun., 1989, 399;
4. (b) J. Broos, M.-N. Martin, I. Rouwenhorst, W. Verboom and D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas, 1991, 110, 222;
5. (c) J. Broos, I. K. Sakodinskaya, J. F. J. Engbersen, W. Verboom and D. N. Reinhoudt, J. Chem. Soc., Chem. Commun., 1995, 255;
6. (d) J. Broos, R. Arends, G. B. van Dijk, W. Verboom, J. F. J. Engbersen and D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. 1, 1996, 1415;
7. (e) J. F. J. Engbersen, J. Broos, W. Verboom and D. N. Reinhoudt, Pure Appl. Chem., 1996, 68, 2171;
8. (f) D. J. van Unen, J. F. J. Engbersen and D. N. Reinhoudt, Biotechnol. Bioeng., 1998, 59, 553.
9. N. L. St. Clair and M. A. Navia, J. Am. Chem. Soc., 1992, 114, 7314.
10. J. Partridge, G. A. Hutcheon, B. D. Moore and P. J. Halling, J. Am. Chem. Soc., 1996, 118, 12873.
11. K. Xu and A. M. Klibanov, J. Am. Chem. Soc., 1996, 118, 9815.
12. (a) R. A. Persichetti, N. L. St. Clair, J. P. Griffith, M. A. Navia and A. L. Margolin, J. Am. Chem. Soc., 1995, 117, 2732;
13. (b) Y.-F. Wang, K. Yakovlevsky, B. Zhang and A. L. Margolin, J. Org. Chem., 1997, 62, 3488.
14. J. L. Schmitke, C. R. Wescott and A. M. Klibanov, J. Am. Chem. Soc., 1996, 118, 3360.
15. N. Khalaf, P. Govardhan, J. J. Lalonde, R. A. Persichetti, Y. F. Wang and A. L. Margolin, J. Am. Chem. Soc., 1996, 118, 5494.
16. G. Gokel, Crown ethers & cryptands, Royal Society of Chemistry, Cambridge, 1991.
17. In cross-linked crystalline thermolysin three out of eleven lysine residues still remain present. Altus Biologies, Personal communication.
18. T. Sakurai, A. L. Margolin, A. J. Russel and A. M. Klibanov, J. Am. Chem. Soc., 1988, 110, 7236.
19. A. Fersht, Enzyme structure and mechanism, 2nd edn., Freeman, New York, 1985.
20. (a) P. J. Halling, Enzyme Microb. Technol., 1994, 16, 178;
21. (b) F. Secundo, S. Riva and G. Carrea, Tetrahedron: Asymmetry, 1992, 3, 267.
22. K. Ryu and J. S. Dordick, J. Am. Chem. Soc., 1989, 111, 8026.
23. P. A. Fitzpatrick, A. C. U. Steinmetz, D. Ringe and A. M. Klibanov, Proc. Natl. Acad. Sci. USA, 1993, 90, 8653.
24. F. de Jong, D. N. Reinhoudt and C. J. Smit, Tetrahedron Lett., 1976, 1371.
25. L. P. Golovkova, A. I. Telyatnik, V. A. Bidzilya, N. E. Akhmetova and V. I. Konovalova, Theor. Exp. Chem. (Engl. Transl.), 1985, 2, 248.
26. Our earlier studies revealed that it is indeed possible for 18-crown-6 to penetrate into the active site of proteases like subtilisin Carlsberg and α-chymotrypsin. It was observed that the hydroxymethyl-18-crown-6 ester of N-acetyl-D,L-phenylalanine could be transesterified and hydrolyzed enantioselectively using respectively propan-1-ol in cyclohexane and an aqueous buffer. These studies proved that hydroxymethyl-18-crown-6 was located in the active site before it was expelled by the enzyme. J. Broos, Ph.D. Thesis, University of Twente, 1994.