Focusing mutations into the P. fluorescens esterase binding site increases enantioselectivity more effectively than distant mutations

Chemistry and Biology

Volumn 12, Issue 1, 2005, Pages 45-54

  Park, Seongsoon ^a,b   Morley, Krista L ^a   Horsman, Geoff P ^a   Holmquist, Mats ^b   Hult, Karl ^b   Kazlauskas, Romas J ^a  

^a MCGILL UNIVERSITY   (Canada)

^b ALBANOVA UNIVERSITY CENTER   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERASE; METHYL 3 BROMO 2 METHYLPROPANOATE; METHYL 3-BROMO-2-METHYLPROPANOATE; PROPIONIC ACID DERIVATIVE;

ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ENZYMOLOGY; GENETICS; KINETICS; METABOLISM; MUTAGENESIS; MUTATION; PSEUDOMONAS FLUORESCENS; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ESTERASES; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MUTAGENESIS; MUTATION; PROPIONATES; PSEUDOMONAS FLUORESCENS; STEREOISOMERISM;

PSEUDOMONAS; PSEUDOMONAS FLUORESCENS;

EID: 12344337569     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.10.012     Document Type: Article

References (62)

1. M.T. Reetz Controlling the enantioselectivity of enzymes by directed evolution: practical and theoretical ramifications Proc. Natl. Acad. Sci. USA 101 2004 5716 5722
2. D.E. Robertson, and B.A. Steer Recent progress in biocatalyst discovery and optimization Curr. Opin. Chem. Biol. 8 2004 141 149
3. P.A. Dalby Optimizing enzyme function by directed evolution Curr. Opin. Struct. Biol. 13 2003 500 505
4. J.R. Cherry, and A.L. Fidantsef Directed evolution of industrial enzymes: an update Curr. Opin. Biotechnol. 14 2003 438 443
5. R. Chen Enzyme engineering: rational redesign versus directed evolution Trends Biotechnol. 19 2001 13 14
6. U.T. Bornscheuer, and M. Pohl Improved biocatalysts by directed evolution and rational protein design Curr. Opin. Chem. Biol. 5 2001 137 143
7. K.-E. Jaeger, T. Eggert, A. Eipper, and M.T. Reetz Directed evolution of an enantioselective lipase Appl. Microbiol. Biotechnol. 55 2001 519 530
8. I.P. Petrounia, and F.H. Arnold Designed evolution of enzymatic properties Curr. Opin. Biotechnol. 11 2000 325 330
9. F.H. Arnold Directed evolution - creating biocatalysts for the future Chem. Eng. Sci. 51 1996 5091 5102
10. F.H. Arnold Design by directed evolution Acc. Chem. Res. 31 1998 125 131
11. M.T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, and K.-E. Jaeger Creation of enantioselective biocatalysts for organic chemistry by in vitro evolution Angew. Chem. Int. Ed. Engl. 36 1997 2830 2832
12. K. Liebeton, A. Zonta, K. Schimossek, M. Nardini, D. Lang, B.W. Dijkstra, M.T. Reetz, and K.-E. Jaeger Directed evolution of an enantioselective lipase Chem. Biol. 7 2000 709 718
13. O. May, P.T. Nguyen, and F.H. Arnold Inverting enantioselectivity by directed evolution of hydantoinase for improved production of l-methionine Nat. Biotechnol. 18 2000 317 320
14. U.T. Bornscheuer, J. Altenbuchner, and H.H. Meyer Directed evolution of an esterase: screening of enzyme libraries based on pH-indicators and a growth assay Bioorg. Med. Chem. 7 1999 2169 2173
15. G.P. Horsman, A.M.F. Liu, E. Henke, U.T. Bornscheuer, and R.J. Kazlauskas Mutations in distant residues moderately increase the enantioselectivity of Pseudomonas fluorescens esterase toward methyl 3-bromo-2-methylpropanoate and ethyl 3-phenylbutyrate Chem. Eur. J. 9 2003 1933 1939
16. M.T. Reetz, C. Torre, A. Eipper, R. Lohmer, M. Hermes, B. Brunner, A. Maichele, M. Bocola, M. Arand, A. Cronin, Y. Genzel, A. Archelas, and R. Furstoss Enhancing the enantioselectivity of an epoxide hydrolase by directed evolution Org. Lett. 6 2004 177 180
17. Y. Koga, K. Kato, H. Nakano, and T. Yamane Inverting enantioselectivity of Burkholderia cepacia KWI-56 lipase by combinatorial mutation and high-throughput screening using single-molecule PCR and in vitro expression J. Mol. Biol. 331 2003 585 592
18. H. Scheib, J. Pleiss, P. Stadler, A. Kovac, A.P. Potthoff, L. Haalck, F. Spener, F. Paltauf, and R.D. Schmid Rational design of Rhizopus oryzae lipase with modified stereoselectivity toward triradylglycerols Protein Eng. 11 1998 675 682
19. D. Rotticci, J.C. Rotticci-Mulder, S. Denman, T. Norin, and K. Hult Improved enantioselectivity of a lipase by rational protein engineering ChemBioChem 2 2001 766 770
20. A. Magnusson, K. Hult, and M. Holmquist Creation of an enantioselective hydrolase by engineered substrate-assisted catalysis J. Am. Chem. Soc. 123 2001 4354 4355
21. R. Rink, J.H.L. Spelberg, R.J. Pieters, J. Kingma, M. Nardini, R.M. Kellogg, B.W. Dijkstra, and D.B. Janssen Mutation of tyrosine residues involved in the alkylation half reaction of epoxide hydrolase from Agrobacterium radiobacter AD1 results in improved enantioselectivity J. Am. Chem. Soc. 121 1999 7417 7418
22. M. Chen-Goodspeed, M.A. Sogorb, F. Wu, and F.M. Raushel Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues Biochemistry 40 2001 1332 1339
23. A.A. Zamyatin Protein volume in solution Prog. Biophys. Mol. Biol. 24 1972 107 123
24. M. Nardini, D.A. Lang, K. Liebeton, K.-E. Jaeger, and B.W. Dijkstra Crystal structure of Pseudomonas aeruginosa lipase in the open conformation. The prototype for family I.1 of bacterial lipases J. Biol. Chem. 275 2000 31219 31225
25. J.D. Cheeseman, A. Tocilj, S. Park, J.D. Schrag, and R.J. Kazlauskas X-Ray crystal structure of an aryl esterase from Pseudomonas fluorescens Acta Crystallogr. D Biol. Crystallogr. 60 2004 1237 1243
26. M. Fromant, S. Blanquet, and P. Plateau Direct random mutagenesis of gene sized DNA fragments using polymerase chain reaction Anal. Biochem. 224 1995 347 353
27. J.E. Ness, S. Kim, A. Gottman, R. Pak, A. Krebber, T.V. Borchert, S. Govindarajan, E.C. Mundorff, and J. Minshull Synthetic shuffling expands functional protein diversity by allowing amino acids to recombine independently Nat. Biotechnol. 20 2002 1251 1255
28. E. Whittle, and J. Shanklin Engineering Δ9-16:0-acyl carrier protein (ACP) desaturase specificity based on combinatorial saturation mutagenesis and logical redesign of the castor Δ9-18:0-ACP desaturase J. Biol. Chem. 276 2001 21500 21505
29. Q.-S. Li, U. Schwaneberg, M. Fischer, J. Schmitt, J. Pleiss, S. Lutz-Wahl, and R.D. Schmid Rational evolution of a medium chain-specific cytochrome P-450 BM-3 variant Biochim. Biophys. Acta 1545 2001 114 121
30. J. Yang, Y. Koga, H. Nakano, and T. Yamane Modifying the chain-length selectivity of the lipase from Burkholderia cepacia KWI-56 through in vitro combinatorial mutagenesis in the substrate-binding site Protein Eng. 15 2002 147 152
31. L.D. Graham, K.D. Haggett, P.A. Jennings, D.S. Le Brocque, and R.G. Whittaker Random mutagenesis of the substrate-binding site of a serine protease can generate enzymes with increased activities and altered primary specificities Biochemistry 32 1993 6250 6258
32. Elferink, V.H.M., Kierkels, J.G.T., Kloosterman, M., and Roskam, J.H. May 1990. Enzyme process for the enantioselective preparation of d-(-)-3-halo-2-methylpropionic acid or derivatives there of and the preparation of captopril therefrom. European patent 369553.
33. Sikorski, J.A., Getman, D.P., Decrescenzo, G.A., Devadas, B., Freskos, J.N., Lu, H.-T., and McDonald, J.J. May 1997. Preparation of N-[2-hydroxy-4-phenyl-3-(sulfonylalkanoylamino)butyl]arylsulfonamides and analogs as retroviral protease inhibitors. World patent 9718205.
34. A. Fadel, and A. Khesrani A straightforward synthesis of both enantiomers of allo-norcoronamic acids and allo-coronamic acids by asymmetric Strecker reaction from alkylcyclopropanone acetals Tetrahedron Asymmetry 9 1998 305 320
35. A. Tait, E. Colorni, and M. Di Bella Stereospecific synthesis of 3-[(2H-1,2,4-benzothiadiazine-1,1-dioxide-3-yl)thio]-2-methylpropanoic acids Tetrahedron Asymmetry 7 1996 2703 2706
36. B.A. Czeskis, and A.M. Moissenkov Synthesis of the S-enantiomer of paniculidine A: absolute R-configuration of the natural paniculidines A and B J. Chem. Soc., Perkin Trans. 1 1 1989 1353 1354
37. M.S. Warren, and S.J. Benkovic Combinatorial manipulation of three key active site residues in glycinamide ribonucleotide transformylase Protein Eng. 10 1997 63 68
38. L.E. Janes, and R.J. Kazlauskas Quick E. A fast spectrophotometric method to measure the enantioselectivity of hydrolases J. Org. Chem. 62 1997 4560 4561
39. L.E. Janes, A.C. Löwendahl, and R.J. Kazlauskas Quantitative screening of hydrolase libraries using pH indicators: identifying active and enantioselective hydrolases Chemistry 4 1998 2317 2324
40. L.E. Janes, A. Cimpoia, and R.J. Kazlauskas Protease-mediated separation of cis and trans diastereomers of 2-(R,S)-benzyloxymethyl-4-(S)-carboxylic acid-1,3-dioxolane methyl ester: intermediates for the synthesis of dioxolane nucleosides J. Org. Chem. 64 1999 9019 9029
41. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih Quantitative analyses of biochemical kinetic resolutions of enantiomers J. Am. Chem. Soc. 104 1982 7294 7299
42. K. Nishizawa, Y. Ohgami, N. Matsuo, H. Kisida, and H. Hirohara Studies of hydrolysis of chiral, achiral and racemic alcohol esters with Pseudomonas cepacia lipase: mechanism of stereospecificity of the enzyme J. Chem. Soc., Perkin Trans. 1 2 1997 1293 1298
43. T. Ema, J. Kobayashi, S. Maeno, T. Sakai, and M. Utaka Origin of the enantioselectivity of lipases explained by a stereo-sensing mechanism operative at the transition state Bull. Chem. Soc. Jpn. 71 1998 443 453
44. C.L. Yaws Chemical Properties Handbook http://www.knovel.com/knovel2/Toc. jsp?BookID=49 2002
45. A.M.F. Liu, N.A. Somers, R.J. Kazlauskas, T.S. Brush, F. Zocher, M.M. Enzelberger, U.T. Bornscheuer, G.P. Horsman, A. Mezzetti, and C. Schmidt-Dannert Mapping the substrate selectivity of new hydrolases using colorimetric screening: lipases from Bacillus thermocatenulatus and Ophiostoma piliferum, esterases from Pseudomonas fluorescens and Streptomyces diastatochromogenes Tetrahedron Asymmetry 12 2001 545 556
46. G. Alagona, C. Ghio, and S. Monti The effect of small substituents on the properties of indole. An ab initio 6-31G* study Theochem 433 1998 203 216
47. D. Rotticci, J.C. Rotticci-Mulder, S. Denman, T. Norin, and K. Hult Improved enantioselectivity of a lipase by rational protein engineering ChemBioChem 2 2001 766 770
48. D. Rotticci, C. Orrenius, K. Hult, and T. Norin Enantiomerically enriched bifunctional sec-alcohols prepared by Candida antarctica lipase B catalysis. Evidence of non-steric interactions Tetrahedron Asymmetry 8 1997 359 362
49. L. Hedstrom, L. Szilagyi, and W.J. Rutter Converting trypsin to chymotrypsin: the role of surface loops Science 255 1992 1249 1253
50. L. Hedstrom Trypsin: a case study in the structural determinants of enzyme specificity Biol. Chem. 377 1996 465 470
51. L. Hedstrom Serine protease mechanism and specificity Chem. Rev. 102 2002 4501 4523
52. E. Szabó, Z. Böcskei, G. Náray-Szabó, and L. Gráf The three-dimensional structure of Asp189Ser trypsin provides evidence for an inherent structural plasticity of the protease Eur. J. Biochem. 263 1999 20 26
53. R.L. Stein Catalysis by human leukocyte elastase: III. Steady-state kinetics for the hydrolysis of p-nitrophenyl esters Arch. Biochem. Biophys. 236 1985 677 680
54. M.R. Arkin, and J.A. Wells Probing the importance of second sphere residues in an esterolytic antibody by phage display J. Mol. Biol. 284 1998 1083 1094
55. A.D. Mesecar, B.L. Stoddard, and D.E. Koshland Jr. Orbital steering in the catalytic power of enzymes: small structural changes with large catalytic consequences Science 277 1997 202 206
56. D.E. Koshland Jr. Conformational changes: how small is big enough? Nat. Med. 4 1998 1112 1114
57. G. DeSantis, K. Wong, B. Farwell, K. Chatman, Z. Zhu, G. Tomlinson, H. Huang, X. Tan, L. Bibbs, and P. Chen Creation of a productive, highly enantioselective nitrilase through gene site saturation mutagenesis (GSSM) J. Am. Chem. Soc. 125 2003 11476 11477
58. K.B. Lipkowitz, C.A. D'Hue, T. Sakamoto, and J.N. Stack Stereocartography: a computational mapping technique that can locate regions of maximum stereoinduction around chiral catalysts J. Am. Chem. Soc. 124 2002 14255 14267
59. N. Guex, A. Diemand, and M.C. Peitsch Protein modelling for all Trends Biochem. Sci 24 1999 364 367
60. R.A. Sayle, and E.J. Milner-White RASMOL: biomolecular graphics for all Trends Biochem. Sci. 20 1995 374 376
61. N. Krebsfänger, F. Zocher, J. Altenbuchner, and U.T. Bornscheuer Characterization and enantioselectivity of a recombinant esterase from Pseudomonas fluorescens Enzym. Microb. Technol. 22 1998 641 646
62. N. Krebsfänger, K. Schierholz, and U.T. Bornscheuer Enantioselectivity of a recombinant esterase from Pseudomonas fluorescens towards alcohols and carboxylic acids J. Biotechnol. 60 1998 105 112