The role of the GGGX motif in determining the activity and enantioselectivity of pig liver esterase towards tertiary alcohols

Biocatalysis and Biotransformation

Volumn 28, Issue 3, 2010, Pages 201-208

  Gall, Markus ^a   Kourist, Robert ^a   Schmidt, Marlen ^a   Bornscheuer, Uwe T ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Enantioselectivity; GGG(A)X motif; Kinetic resolution; Molecular modeling; Pig liver esterase; Tertiary alcohol

Indexed keywords

COMPUTER MODELING; GGG(A)X MOTIF; KINETIC RESOLUTION; PIG LIVER ESTERASE; TERTIARY ALCOHOLS;

ELECTRON TRANSITIONS; LIVER; MOLECULAR MODELING;

ENANTIOSELECTIVITY;

ALANINE; ALCOHOL; GLYCINE; ISOENZYME; PIG LIVER ESTERASE; RECOMBINANT ENZYME; SERINE DEHYDRATASE; TERTIARY ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; ESCHERICHIA COLI; KINETICS; MOLECULAR MODEL; MUTANT; MUTATION; NONHUMAN; PROTEIN EXPRESSION; PROTEIN MOTIF; SITE DIRECTED MUTAGENESIS;

SUIDAE;

EID: 77954292792     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.3109/10242421003753803     Document Type: Article

References (36)

1. Asakawa K, Noguchi N, Takashima S, Nakada M. 2008. Preparation of a new chiral building block containing a benzylic quaternary stereogenic center and a formal total synthesis of (-)-physostigmine. Tetrahedron Asymm 18:2304-2309.
2. Bartsch S, Kourist R, Bornscheuer UT. 2008. Complete inversion of enantioselectivity towards acetylated tertiary alcohols by a double mutant of a Bacillus subtilis esterase. Angew Chem Int Ed. Engl 47:1508-1511.
3. Bencharit S, Morton CL, Hyatt JL, Kuhn P, Danks MK, Potter PM, Redinbo MR. 2003. Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug Tacrine: from binding promiscuity to selective inhibition. Chem Biol 10:341-349.
4. Bennett-Lovsey RM, Herbert AD, Sternberg MJE, Kelley LA. 2008. Exploring the extremes of sequence/structure space with ensemble fold recognition in the program Phyre. Proteins 70:611-625.
5. Bornscheuer UT, Kazlauskas RJ. 2006. Hydrolases in organic synthesis. 2nd ed. Weinheim: Wiley-VCH.
6. B ö ttcher D, Br ü sehaber E, Doderer K, Bornscheuer UT. 2007. Functional expression of the "/-isoenzyme of pig liver carboxyl esterase in Escherichia coli. Appl Microbiol Biotechnol 73, 1282-1289.
7. Br ü sehaber E, B ö ttcher D, Musidlowska-Persson A, Albrecht D, Hecker M, Doderer K, Bornscheuer UT. 2007. Identifi cation of pig liver esterase variants by tandem mass spectroscopy analysis and their characterization. Appl Mcrobiol Biotechnol 76:853-859.
8. Chen C, Fujimoto Y, Girdaukas G, Sih CJ. 1982. Quantitative analyses of biochemical kinetic resolutions. J Am Chem Soc 104:7294-7299.
9. Cozzi PG, Hilgraf R, Zimmermann N. 2007. Enantioselective catalytic formation of quaternary stereogenic centers. Eur J Org Chem. 5969-5994.
10. Csuk R, Woeste B. 2008. A chemoenzymatic approach to (+)-pilocarpine. Tetrahedron 64:9384-9387
11. Dom í nguez de Mar í a P, Garc í a Burgos CA, Bargeman G, van Gemert RW. 2007. Pig liver esterase (PLE) as biocatalyst in organic synthesis: from nature to cloning and to practical applications. Synthesis 10:1439-1452.
12. Hari Krishna S, Persson M, Bornscheuer UT. 2002. Enantioselective transesterifi cation of a tertiary alcohol by lipase A from Candida antarctica. Tetrahedron Asymm 13:2693-2696.
13. Heikinheimo P, Goldman A, Jeffries C, Ollis DL. 1999. Of barn owls and bankers: a lush variety of a/p hydrolases. Structure 7:141-146.
14. 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. Protein Eng Des Sel 20:125-131.
15. Henke E, Pleiss J, Bornscheuer UT. 2002. Activity of lipases and esterases towards tertiary alcohols: insights into structure-function relationships. Angew Chem Int Ed Engl 41:3211-3213.
16. Henke E, Bornscheuer UT, Schmid RD, Pleiss J. 2003. A molecular mechanism of enantiorecognition of tertiary alcohols by carboxylesterases. ChemBioChem 4:485-493.
17. Hermann M, Kietzmann MU, Ivancic M, Zenzmair C, Luiten RGM, Skranc W, Wubbolts M, Winkler M, Birner-Gruenberger R, Pichler H, Schwab H. 2008. Alternative pig liver esterase (APLE)-cloning, identifi cation and functional expression in Pichia pastoris of a versatile new biocatalyst. J Biotechnol 133:301-310.
18. Hou C, Adachi S. 2005. Handbook of industrial biocatalysis. Boca Raton (FL): CRC Taylor & Francis.
19. Hummel A, Br ü sehaber E, B ö ttcher D, Trauthwein H, Doderer K, Bornscheuer UT. 2007. Isoenzymes of pig-liver esterase reveal striking differences in enantioselectivities. Angew Chem Int Ed. Engl 46: 8492-8494.
20. Kourist R, Bartsch S, Bornscheuer U T. 2007a. Highly enantioselec-tive synthesis of arylaliphatic tertiary alcohols using mutants of an esterase from Bacillus subtilis. Adv Synth Catal 349:1393-1398.
21. Kourist R, Hari Krishna S, Patel JS, Bartnek F, Hitchman TS, Weiner DP, Bornscheuer UT. 2007b. Identifi cation of a metage-nome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols. Org Biomol Chem 5:3310-3313.
22. Kourist R, Dom í nguez de Mar í a P, Bornscheuer UT. 2008a. Enzymatic synthesis of optically active tertiary alcohols: expanding the biocatalysis toolbox. ChemBioChem 9:491-498.
23. Kourist R, Nguyen G, Str ü bing D, B ö ttcher D, Liebeton K, Naumer C, Eck J, Bornscheuer UT. 2008b. Hydrolase-cata-lyzed stereoselective preparation of protected α, α-dialkyl-α-hydroxycarboxylic acids. Tetrahedron Asymm 19:1839-1843.
24. Krieger E, Darden T, Nabuurs SB, Finkelstein A, Vriend G. 2004. Making optimal use of empirical energy functions: force-fi eld parameterization in crystal space. Proteins 57:678-683.
25. Lange S, Musidlowska A, Schmidt-Dannert C, Schmitt J, Born-scheuer U T. 2001. Cloning, functional expression, and characterization of recombinant pig liver esterase. ChemBioChem 2:576-582.
26. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. 1998. Automated docking using a lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639-1662.
27. Musidlowska A, Lange S, Bornscheuer UT. 2001. By overexpres-sion in the yeast Pichia pastoris to enhanced enantioselectivity: new aspects in the application of pig liver esterase. Angew Chem Int Ed Engl 40:2851-2853.
28. Musidlowska-Persson A, Bornscheuer UT. 2003. Site directed mutagenesis of recombinant pig liver esterase yields mutants with altered enantioselectivity. Tetrahedron Asymm 14: 1341-1344.
29. Nguyen G, Kourist R, Paravidino M, Hummel A, Rehdorf J, Orru RVA, Hanefeld U, Bornscheuer UT. 2010. An enzymatic toolbox for the kinetic resolution of 2-(pyridinyl)but-3-yn-2-ols and tertiary cyanohydrins. Eur J Org Chem. DOI: dx.doi.org/10.1002/ejoc.201000193.
30. Ollis DL, Cheah E, Cygler M, Dijkstram B, Frolow F, Franken SM, Harel M, Remington, S. James, Silman I, Schrag J, Suss-man JL, Verschueren KHG, Goldman A. 1992. The α/β hydro-lase fold. Protein Eng 5:197-211.
31. Pleiss J, Fischer M, Peiker M, Thiele C, Schmid RD. 2000. Lipase engineering database: understanding and exploiting sequence-structure-function relationships. J Mol Catal B: Enzym 11: 491-508.
32. Sanner MF. 1999. Python: a programming language for software integration and development. J Mol Graph Model 17: 57-61.
33. Schlacher A, Stanzer T, Ospiran I, Mischitz M, Klingsbichel E, Faber K, Schwab H. 1998. Detection of a new enzyme for stereoselective hydrolysis of linalyl acetate using simple plate assays for the characterization of cloned esterases from Burkhol-deria gladioli. J Biotechnol 62:47-54.
34. Schmidt M, Henke E, Heinze B, Kourist R, Hidalgo A, Born-scheuer UT. 2007. A versatile esterase from Bacillus subtilis: cloning, expression, characterization, and its application in bio-catalysis. Biotechnol J 2:249-253.
35. Wang J, Cieplak P, Kollman PA. 2000. How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J Comput Chem 21:1049-1074.
36. Zutter U, Iding H, Spurr P, Wirz B. 2008. New, effi cient synthesis of oseltamivir phosphate (Tamifl u) via enzymatic desym-metrization of a meso-1,3-cyclohexanedicarboxylic acid diester. J Org Chem 73:4895-4902.