Control of stereoselectivity in an enzymatic reaction by backdoor access

Angewandte Chemie - International Edition

Volumn 45, Issue 15, 2006, Pages 2469-2472

  Wombacher, Richard ^a   Keiper, Sonja ^a   Suhm, Sandra ^a   Serganov, Alexander ^b   Patel, Dinshaw J ^b   Jäschke, Andres ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

Cycloaddition; Enantioselectivity; Enzyme catalysis; Ribozymes

Indexed keywords

CYCLOADDITION; ENANTIOSELECTIVITY; ENZYME CATALYSIS; RIBOZYMES;

AROMATIC COMPOUNDS; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ENZYME IMMOBILIZATION;

RIBOZYME;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM; PROTEIN TERTIARY STRUCTURE; STEREOISOMERISM;

CATALYSIS; MODELS, MOLECULAR; PROTEIN STRUCTURE, TERTIARY; RNA, CATALYTIC; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 33646161586     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503280     Document Type: Article

References (37)

1. E. Fischer, Ber. Dtsch. Chem. Ges. 1894, 27, 2985.
2. A. G. Ogston, Nature 1948, 162, 963.
3. A. D. Mesecar, D. E. Koshland, Jr., Nature 2000, 403, 614.
4. R. S. Shallenberger, T. E. Acree, Nature 1967, 216, 480.
5. M. T. Reetz, Proc. Natl. Acad. Sci. USA 2004, 101, 5716.
6. F. H. Arnold, Nature 2001, 409, 253.
7. O. May, P. T. Nguyen, F. H. Arnold, Nat. Biotechnol. 2000, 18, 317.
8. R. C. Wade, B. A. Luty, E. Demchuk, J. D. Madura, M. E. Davis, J. M. Briggs, J. A. McCammon, Nat. Struct. Biol. 1994, 1, 65.
9. K. Schleinkofer, Sudarko, P. J. Winn, S. K. Lüdemann, R. C. Wade, EMBO Rep. 2005, 6, 584.
10. R. G. Yount, D. Lawson, I. Rayment, Biophys. J. 1995, 68, 44S.
11. A. Ostermann, R. Waschipky, F. G. Parak, G. U. Nienhaus, Nature 2000, 404, 205.
12. G. Koellner, G. Kryger, C. B. Millard, I. Silman, J. L. Sussman, T. Steiner, J. Mol. Biol. 2000, 296, 713.
13. B. Seelig, A. Jäschke, Chem. Biol. 1999, 6, 167.
14. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. 2002, 114, 1747;
15. Angew. Chem. Int. Ed. 2002, 41, 1668.
16. E. M. Stocking, R. M. Williams, Angew. Chem. 2003, 115, 3186;
17. Angew. Chem. Int. Ed. 2003, 42, 3078.
18. T. Ose, K. Watanabe, T. Mie, M. Honma, H. Watanabe, M. Yao, H. Oikawa, I. Tanaka, Nature 2003, 422, 185.
19. C. R. Guimaraes, M. Udier-Blagovic, W. L. Jorgensen, J. Am. Chem. Soc. 2005, 127, 3577.
20. B. Seelig, S. Keiper, F. Stuhlmann, A. Jäschke, Angew. Chem. 2000, 112, 4764;
21. Angew. Chem. Int. Ed. 2000, 39, 4576.
22. F. Stuhlmann, A. Jäschke, J. Am. Chem. Soc. 2002, 124, 3238.
23. A. Serganov, S. Keiper, L. Malinina, V. Tereshko, E. Skripkin, C. Höbartner, A. Polonskaia, A. T. Phan, R. Wombacher, R. Micura, Z. Dauter, A. Jäschke, D. J. Patel, Nat. Struct. Mol. Biol. 2005, 12, 218.
24. Competition experiments clearly support the intramolecular nature of the reaction with the tethered substrate. Addition of 2, 4, and 8 equiv of ribozyme to 1 equiv of anthracenehexa-(ethylene glycol)-ribozyme had no effect on the initial rate of the Diels-Alder reaction.
25. -1).
26. T. Hermann, P. Auffinger, E. Westhof, Eur. Biophys. J. 1998, 27, 153.
27. C. Jeppesen, J. Y. Wong, T. L. Kuhl, J. N. Israelachvili, N. Mullah, S. Zalipsky, C. M. Marques, Science 2001, 293, 465.
28. It should be noted that this situation provides strong experimental support for the four-location model of stereoselective recognition by Mesecar and Koshland (see Ref. [3]).
29. M. K. Gilson, T. P. Straatsma, J. A. McCammon, D. R. Ripoll, C. H. Faerman, P. H. Axelsen, I. Silman, J. L. Sussman, Science 1994, 263, 1276.
30. J. D. Lawson, E. Pate, I. Rayment, R. G. Yount, Biophys. J. 2004, 86, 3794.
31. U. T. Bornscheuer, R. J. Kazlauskas, Angew. Chem. 2004, 116, 6156;
32. Angew. Chem. Int. Ed. 2004, 43, 6032.
33. Y. Shi, Trends Genet. 2004, 20, 445.
34. D. R. Klopfenstein, R. D. Vale, S. L. Rogers, Cell 2000, 103, 537.
35. G. J. Bartlett, N. Borkakoti, J. M. Thornton, J. Mol. Biol. 2003, 331, 829.
36. L. C. James, D. S. Tawfik, Protein Sci. 2001, 10, 2600.
37. P. J. O'Brien, D. Herschlag, Chem. Biol. 1999, 6, 91.