The role of conformational flexibility of enzymes in the discrimination between amino acid and ester substrates for the subtilisin-catalyzed reaction in organic solvents

Bioorganic Chemistry

Volumn 32, Issue 6, 2004, Pages 504-515

  Watanabe, Keiichi ^a   Yoshida, Takashi ^a   Ueji, Shin Ichi ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

Enantioselectivity; Enzyme flexibility; ESR spectroscopy; Organic solvent; Subtilisin

Indexed keywords

AMINO ACID; DIMETHYL SULFOXIDE; ESTER DERIVATIVE; ORGANIC SOLVENT; SUBTILISIN;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CORRELATION ANALYSIS; ELECTRON SPIN RESONANCE; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME MECHANISM; MICHAELIS MENTEN KINETICS; NONHUMAN; PARAMETER; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN FUNCTION;

AMINO ACIDS; CATALYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; ESTERS; KINETICS; OCTANES; PROTEIN CONFORMATION; SOLVENTS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SUBTILISINS;

EID: 8644246761     PISSN: 00452068     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioorg.2004.05.001     Document Type: Article

References (40)

1. Carrea G., Riva S. Angew. Chem. Int. Ed. 39:2000;2226-2254
2. Klibanov A.M. Nature. 409:2001;241-246
3. Bordusa F. Chem. Rev. 102:2002;4817-4867
4. Zaks A., Klibanov A.M. Proc. Natl. Acad. Sci. USA. 82:1985;3192-3196
5. Chen C.-S., Sih C.J. Angew. Chem. Int. Ed. 28:1989;695-707
6. Dordick J.S. Enzyme Microb. Technol. 11:1989;194-211
7. Khmelnitsky Y.L., Welch S.H., Clark D.S., Dordick J.S. J. Am. Chem. Soc. 116:1994;2647-2648
8. Okamoto T., Ueji S. Chem. Commun. 1999;939-940
9. Watanabe K., Yoshida T., Ueji S. Chem. Commun. 2001;1260-1261
10. Ueji S., Nishimura M., Kudo R., Matsumi R., Watanabe K., Ebara Y. Chem. Lett. 2001;912-913
11. Ueji S., Sakamoto H., Watanabe K., Okamoto T., Mori S. Bull. Chem. Soc. Jpn. 75:2002;2239-2240
12. Fitzpatrick P.A., Klibanov A.M. J. Am. Chem. Soc. 113:1991;3166-3171
13. Parida S., Dordick J.S. J. Org. Chem. 58:1993;3238-3244
14. Carrea G., Ottolina G., Riva S. Trends Biotechnol. 13:1995;63-70
15. Ueji S., Taniguchi T., Okamoto T., Watanabe K., Ebara Y., Ohta H. Bull. Chem. Soc. Jpn. 76:2003;399-403
16. Phillips R.S. Trends Biotechnol. 14:1996;13-16
17. Galunsky B., Ignatova S., Kasche V. Biochim. Biophys. Acta. 1343:1997;130-138
18. Yasufuku Y., Ueji S. Bioorg. Chem. 25:1997;88-99
19. Wescott C.R., Klibanov A.M. Biochim. Biophys. Acta. 1206:1994;1-9
20. Reetz M.T., Zonta A., Schimossek K., Liebeton K., Jaeger K.-E. Angew. Chem. Int. Ed. 36:1997;2830-2832
21. Reetz M.T., Jaeger K.-E. Chem. Eur. J. 6:2000;407-412
22. Okahata Y., Fujimoto Y., Ijiro K. J. Org. Chem. 60:1995;2244-2250
23. Fishman A., Basheer S., Shatzmiller S., Cogan U. Biotechnol. Lett. 20:1998;535-538
24. Ueji S., Tanaka H., Hanaoka T., Ueda A., Watanabe K., Kaihatsu K., Ebara Y. Chem. Lett. 2001;1066-1067
25. Ueji S., Ueda A., Tanaka H., Watanabe K., Okamoto T., Ebara Y. Biotechnol. Lett. 25:2003;83-87
26. Theil F. Tetrahedron. 56:2000;2905-2919
27. Broos J., Visser A.J.W.G., Engbersen J.F.J., Verboom W., Hoek A., Reinhoudt D.N. J. Am. Chem. Soc. 117:1995;12657-12663
28. Broos J. Biocat. Biotrans. 20:2002;291-295
29. Dhaon M.K., Olsen R.K., Ramasamy K. J. Org. Chem. 47:1982;1962-1965
30. Witiak D.T., Ho T.C.-L., Hackney R.E. J. Med. Chem. 11:1968;1086-1089
31. Morrisett J.D., Broomfield C.A. J. Biol. Chem. 247:1972;7224-7231
32. Affleck R., Xu Z.-F., Suzawa V., Focht K., Clark D.S., Dordick J.S. Proc. Natl. Acad. Sci. USA. 89:1992;1100-1104
33. Zaks A., Klibanov A.M. J. Biol. Chem. 263:1988;8017-8021
34. Kitaguchi H., Itoh I., Ono M. Chem. Lett. 1990;1203-1206
35. Bovara R., Carrea G., Ottolina G., Riva S. Biotechnol. lett. 15:1993;937-942
36. Kawashiro K., Sugahara H., Sugiyama S., Hayashi H. Biotechnol. Lett. 17:1995;1161-1166
37. Boutelje J., Hjalmarsson M., Hult K., Lindback M., Norin T. Bioorg. Chem. 16:1988;364-375
38. Watanabe K., Ueji S. Biotechnol. Lett. 22:2000;599-603
39. Watanabe K., Ueji S. Biocat. Biotrans. 19:2001;281-299
40. Watanabe K., Ueji S. Soc. J. Chem. Perkin Trans. 1:2001;1386-1390