Pseudomonas putida esterase contains a GGG(A)X-motif confering activity for the kinetic resolution of tertiary alcohols

Applied Microbiology and Biotechnology

Volumn 93, Issue 3, 2012, Pages 1119-1126

  Rehdorf, Jessica ^a,b   Behrens, Geoffrey A ^a   Nguyen, Giang Son ^a   Kourist, Robert ^a   Bornscheuer, Uwe T ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b BRAIN AG   (Germany)

Author keywords

Biocatalysis; Carboxylesterases; GGG(A)X motif; Kinetic resolution; Tertiary alcohols

Indexed keywords

BIOCATALYSIS; CARBOXYLESTERASES; GGG(A)X-MOTIF; KINETIC RESOLUTION; TERTIARY ALCOHOLS;

AFFINITY CHROMATOGRAPHY; BACTERIA; CLONING; ENZYMES; ESCHERICHIA COLI; ESTERS; HYDROLYSIS; KINETICS;

VOLATILE FATTY ACIDS;

4 HYDROXYACETOPHENONE; 4 HYDROXYPHENYL ACETATE; ACETIC ACID DERIVATIVE; ALCOHOL; BACTERIAL ENZYME; BUTYRIC ACID DERIVATIVE; CARBOXYLESTERASE; DELTA VALEROLACTONE; EPSILON CAPROLACTONE; LACTONE; UNCLASSIFIED DRUG;

ALCOHOL; CATALYSIS; CATALYST; COLIFORM BACTERIUM; ENZYME ACTIVITY; HOMOGENEITY; HYDROLYSIS; PHYSIOLOGICAL RESPONSE;

AFFINITY CHROMATOGRAPHY; AMINO ACID SEQUENCE; ARTICLE; BIOCATALYSIS; CLONING; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME METABOLISM; ENZYME PURIFICATION; ESCHERICHIA COLI; HYDROLYSIS; MOLECULAR MODEL; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PH; PROTEIN DETERMINATION; PROTEIN EXPRESSION; PROTEIN MOTIF; PSEUDOMONAS PUTIDA; TEMPERATURE DEPENDENCE;

ALCOHOLS; AMINO ACID MOTIFS; AMINO ACID SEQUENCE; BIOCATALYSIS; CLONING, MOLECULAR; ESCHERICHIA COLI; ESTERASES; KINETICS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PSEUDOMONAS PUTIDA; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, DNA; SUBSTRATE SPECIFICITY;

ESCHERICHIA COLI; PSEUDOMONAS PUTIDA;

EID: 84856365546     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3464-3     Document Type: Article

References (34)

1. Arpigny JL, Jäger KE (1999) Bacterial lipolytic enzymes: classification and properties. Biochem J 343:177-183 (Pubitemid 29473893)
2. Bornscheuer UT (2002) Microbial carboxyl esterases: classification, properties and application in biocatalysis. FEMS Microbiol Rev 26:73-81 (Pubitemid 34454776)
3. Bornscheuer UT, Kazlauskas RJ (2005) Hydrolases in organic synthesis-regio- and stereoselective biotransformations, 2nd edn. Wiley-VCH, Weinheim
4. Böttcher D, Brüsehaber E, Doderer K, Bornscheuer UT (2007) Functional expression oft he gamma-isoenzyme of pig liver carboxyl esterase in Escherichia coli. Appl Microbiol Biotechnol 73:1282-1289 (Pubitemid 46089500)
5. Byun J-S, Rhee J-K, Kim ND, Yoon J, Kim D-U, Koh E, Oh J-W, Cho H-S (2007) Crystal structure of hyperthermophilic esterase EstE1 and the relationship between its dimerization and thermostability properties. BMC Struct Biol 7:1-11 (Pubitemid 47206832)
6. Chen C-S, Fujimoto Y, Girdaukas G, Sih CJ (1982) Quantitative analysis of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104:7294-7299
7. Drauz K, Waldmann H (eds) (1995) Enzyme Catalysis in Organic Synthesis. Wiley-VCH, Weinheim
8. Duan Y, Wu C, Chowdhury S, Lee MC, Xiong G, Zhang W, Yang R, Cieplak P, Luo R, Lee T (2003) A point-charge force field for molecular mechanics simulations of proteins. J Comput Chem 24:1999-2012
9. Essman U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG (1995) A smooth particle mesh Ewald method. J Chem Phys B 103:8577-8593
10. Faber K (2000) Biotransformations in Organic Chemistry. Springer, Berlin
11. Heinze B, Kourist R, Fransson L, Hult K, Bornscheuer UT (2007) Highly enantioselective kinetic resolution of two tertiary alcohols using mutants of an esterase from Bacillus subtilis. Prot Eng Des Sel 20:123-131 (Pubitemid 46536746)
12. Henke E, Pleiss J, Bornscheuer UT (2002) Activity of lipases and esterases towards tertiary alcohols: insights into structure-function relationships. Angew Chem Int Ed 41:3211-3213 (Pubitemid 35014389)
13. Henke E, Bornscheuer UT, Schmid RD, Pleiss J (2003) A molecular mechanism of enantiorecognition of tertiary alcohols by carboxylesterases. ChemBioChem 4:485-493 (Pubitemid 36749618)
14. Hotta Y, Ezaki S, Atomi H, Imanaka T (2002) Extremely stable and versatile carboxylesterase from a hyperthermophilic archaeon. Appl Environ Microbiol 68:3925-3931 (Pubitemid 34836705)
15. Hummel A, Brüsehaber E, Böttcher D, Trauthwein H, Doderer K, Bornscheuer UT (2007) Isoenzyes of pig-liver esterase reveal striking differences in enantioselectivities. Angew Chem Int Ed 46:8492-8494 (Pubitemid 350114969)
16. Jones RM, Collier LS, Neidle EL, Williams PA (1999) AreABC genes determine the catabolism of aryl esters in Acinetobacter sp. strain ADP1. J Bacteriol 181:4568-4575 (Pubitemid 29357938)
17. Konagurthu AS, Whisstock JC, Stuckey PJ, Lesk AM (2006) MUSTANG: a multiple structural alignment algorithm. Proteins 64:559-574 (Pubitemid 44100724)
18. Kourist R, Bornscheuer UT (2011) Biocatalytic synthesis of optically active tertiary alcohols. Appl Microbiol Biotechnol. doi: 10.1007/s00253-011- 3418-9
19. Kourist R, Bartsch S, Bornscheuer UT (2007a) Highly enantioselective synthesis of arylaliphatic tertiary alcohols using mutants of an esterase from Bacillus subtilis. Adv Synth Catal 349:1393-1398
20. Kourist R, Krishna SH, Patel JS, Bartnek F, Hitchman TS, Weiner DP, Bornscheuer UT (2007b) Identification of a metagenome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols. Org Biomol Chem 5:3310-3313 (Pubitemid 47519068)
21. Krieger E, Darden T, Nabuurs S, Finkelstein A, Vriend G (2004) Making optimal use of empirical energy function: force field parameterization in crystal space. Proteins 57:678-683 (Pubitemid 39626989)
22. Krieger E, Nielsen JE, Spronk CA, Vriend G (2006) Fast empirical pKa prediction by Ewald summation. J Mol Graph Model 25:481-486 (Pubitemid 44667584)
23. Krishna SH, Persson M, Bornscheuer UT (2002) Enantioselective transesterification of a tertiary alcohol by lipase A from Candida antarctica. Tetrahedron-Asymmetry 13:2693-2696 (Pubitemid 35454025)
24. Nguyen G-S, Kourist R, Paravidino M, Hummel A, Rehdorf J, Orru RVA, Hanefeld U, Bornscheuer UT (2010) An enzymatic toolbox for the kinetic resolution of 2-(pyridin-x-yl)but-3-yn-2-ols and tertiary cyanohydrins. Eur J Org Chem 2010:2753-2758
25. O'Hagan D, Zaidi NA (1994) The resolution of tertiary α-acetylene-acetate esters by the lipase from Candida cylindracea. Tetrahedron-Asymmetry 5:1111-1118 (Pubitemid 24208261)
26. O'Hagan D, Zaidi NA, Lamont RB (1993) The synthesis of (R)-γ-phenyl-γ-(trifluoromethyl)butyrolactone and (2R,3S)-1,1,1-trifluoro-2-methoxy-2-phenyl-3,4-epoxybutane in homochiral form. Tetrahedron-Asymmetry 4:1703-1708 (Pubitemid 23208601)
27. Patel RN (ed) (2000) Stereoselective Biocatalysis. Marcel Dekker, New York
28. Rehdorf J, Kirschner A, Bornscheuer UT (2007) Cloning, expression and characterization of a Baeyer-Villiger monooxygenase from Pseudomonas putida KT2440. Biotechnol Lett 29:1393-1398 (Pubitemid 47205848)
29. Rehdorf J, Zimmer CL, Bornscheuer UT (2009) Cloning, expression, characterization and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from P. putida JD1. Appl Environ Microbiol 75:3106-3114
30. Sambrook J, Russell DW (2001) Molecular Cloning: A Laboratory Manual. Cold Spring Harbour Laboratory, New York
31. Schliessmann A, Hidalgo A, Berenguer J, Bornscheuer UT (2009) Increased enatioselectivity by engineering bottleneck mutants in an esterase from Pseudomonas fluorescens. ChemBioChem 10:2920-2923
32. Schmidt M, Hasenpusch D, Kähler M, Kirchner U, Wiggenhorn K, Langel W, Bornscheuer UT (2006) Directed evolution of an esterase from Pseudomonas fluorescens yields a mutant with excellent enantioselectivity and activity for the kinetic resolution of a chiral building block. ChemBioChem 7:805-809 (Pubitemid 43764190)
33. Schmidt M, Henke E, Heinze B, Kourist R, Hidalgo A, Bornscheuer UT (2007) A versatile esterase from Bacillus subtilis: cloning, expression, characterization and ist application in biocatalysis. Biotechnol J 2:249-253 (Pubitemid 46738878)
34. Stymiest J, Bagutski V, French R, Aggarwal V (2008) Enantiodivergent conversion of chiral secondary alcohols into tertiary alohols. Nature 456:778-782