Enantioselectivity of Candida rugosa lipases (Lip1, Lip3, and Lip4) towards 2-bromo phenylacetic acid octyl esters controlled by a single amino acid

Biotechnology and Bioengineering

Volumn 108, Issue 8, 2011, Pages 1749-1756

  Piamtongkam, Rungtiwa ^a,b,c,d   Duquesne, Sophie ^a,b,c   Bordes, Florence ^a,b,c   Barbe, Sophie ^a,b,c   André, Isabelle ^a,b,c   Marty, Alain ^a,b,c   Chulalaksananukul, Warawut ^d  

^a INSA   (France)

^b CNRS   (France)

^c UMR792 INGÉNIERIE DES SYSTÈMES BIOLOGIQUES ET DES PROCÉDÉS   (France)

^d CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Candida rugosa; Enantioselectivity; Lipase; Rational engineering; Yarrowia lipolytica

Indexed keywords

ACID ESTER; ACTIVE SITE; AMINO ACID RESIDUES; ATOMIC LEVELS; CANDIDA RUGOSA; CANDIDA RUGOSA LIPASE; CHEMICAL INTERMEDIATES; ENANTIODISCRIMINATION; ENANTIOMER DISCRIMINATION; HIGH ENANTIOSELECTIVITY; ISOFORMS; PHARMACEUTICAL INDUSTRY; PHENYLACETIC ACID; PRELIMINARY MODELING; RATIONAL ENGINEERING; SEQUENCE HOMOLOGY; SITE DIRECTED MUTAGENESIS; STERIC HINDRANCES; STRUCTURE ANALYSIS; TETRAHEDRAL INTERMEDIATES; YARROWIA LIPOLYTICA;

ACETIC ACID; AMINO ACIDS; CANDIDA; CHIRALITY; ENANTIOMERS; ESTERIFICATION; ESTERS; LIPASES; YEAST;

ENANTIOSELECTIVITY;

2 BROMO PHENYLACETIC ACID OCTYL ESTER; ALANINE; FUNGAL ENZYME; GLYCINE; LEUCINE; LIPASE1; LIPASE3; LIPASE4; PHENYLACETIC ACID; PHENYLALANINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CANDIDA RUGOSA; DRUG HYDROLYSIS; ENANTIOSELECTIVITY; ENZYME STRUCTURE; NONHUMAN; SITE DIRECTED MUTAGENESIS; STRUCTURE ANALYSIS; YARROWIA LIPOLYTICA;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; AMINO ACIDS; CANDIDA; CATALYTIC DOMAIN; ESTERS; LIPASE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; PHENYLACETATES; PROTEIN ENGINEERING; SEQUENCE ALIGNMENT; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

CANDIDA RUGOSA; YARROWIA LIPOLYTICA;

EID: 79959252484     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.23124     Document Type: Article

References (22)

1. Akoh CC, Lee GC, Shaw JF. 2004. Protein engineering and applications of Candida rugosa lipase isoforms. Lipids 39(6): 513-526.
2. Bordes F, Fudalej F, Dossat V, Nicaud JM, Marty A. 2007. A new recombinant protein expression system for high-throughput screening in the yeast Yarrowia lipolytica J Microbiol Methods 70(3): 493-502.
3. Bordes F, Cambon E, Dossat-Letisse V, Andre I, Croux C, Nicaud JM, Marty A. 2009. Improvement of Yarrowia lipolytica lipase enantioselectivity by using mutagenesis targeted to the substrate binding site. Chembiochem 10(10): 1705-1713.
4. Cambon E, Piamtongkam R, Bordes F, Duquesne S, Laguerre S, Nicaud J, Marty A. 2010. A new Yarrowia lipolytica expression system: An efficient tool for rapid and reliable kinetic analysis of improved enzymes. Enzyme Microb Technol 47: 91-96.
5. Cygler M, Grochulski P, Kazlauskas RJ, Schrag JD, Bouthillier F, Rubin B, Serreqi AN, Gupta AK. 1994. A structural basis for the chiral preferences of lipases. J Am Chem Soc 116(8): 3180-3186.
6. de Castro MS, Sinisterra Gago J. 1998. Lipase-catalyzed synthesis of chiral amides. A systematic study of the variables that control the synthesis. Tetrahedron 54(12): 2877.
7. DeLano WL. 2002. The PyMOL Molecular Graphics System, on World Wide Web. San Carlos, CA, USA.
8. Grochulski P, Li Y, Schrag JD, Cygler M. 1994. Two conformational states of Candida rugosa lipase. Protein Sci 3(1): 82-91.
9. Guieysse D, Salagnad C, Monsan P, Remaud-Simeon M. 2001. Resolution of 2-bromo-o-tolyl-carboxylic acid by transesterification using lipases from Rhizomucor miehei and Pseudomonas cepacia Tetrahedron Asymmetry 12(17): 2473.
10. Kim MG, Lee EG, Chung BH. 2000. Improved enantioselectivity of Candida rugosa lipase towards ketoprofen ethyl ester by a simple two-step treatment. Process Biochem 35: 977-982.
11. Kramer B, Rarey M, Lengauer T. 1999. Evaluation of the FLEXX incremental construction algorithm for protein-ligand docking. Proteins 37(2): 228-241.
12. Lafaquiere V, Barbe S, Puech-Guenot S, Guieysse D, Cortes J, Monsan P, Simeon T, Andre I, Remaud-Simeon M. 2009. Control of lipase enantioselectivity by engineering the substrate binding site and access channel. Chembiochem 10(17): 2760-2771.
13. Lee LC, Chen YT, Yen CC, Chiang TC, Tang SJ, Lee GC, Shaw JF. 2007. Altering the substrate specificity of Candida rugosa LIP4 by engineering the substrate-binding sites. J Agric Food Chem 55(13): 5103-5108.
14. Manetti F, Mileto D, Corelli F, Soro S, Palocci C, Cernia E, D'Acquarica I, Lotti M, Alberghina L, Botta M. 2000. Design and realization of a tailor-made enzyme to modify the molecular recognition of 2-arylpropionic esters by Candida rugosa lipase. Biochim Biophys Acta 1543(1): 146-158.
15. Muralidhar RV, Chirumamilla RR, Ramachandran VN, Marchant R, Nigam P. 2002. Resolution of (RS)-proglumide using lipase from Candida cylindraceae Bioorg Med Chem 10(5): 1471-1475.
16. Nicaud JM, Madzak C, van den Broek P, Gysler C, Duboc P, Niederberger P, Gaillardin C. 2002. Protein expression and secretion in the yeast Yarrowia lipolytica. FEMS Yeast Res 2(3): 371-379.
17. Pleiss J, Fischer M, Schmid RD. 1998. Anatomy of lipase binding sites: The scissile fatty acid binding site. Chem Phys Lipids 93(1-2): 67-80.
18. Rarey M, Kramer B, Lengauer T, Klebe G. 1996a. A fast flexible docking method using an incremental construction algorithm. J Mol Biol 261(3): 470-489.
19. Rarey M, Wefing S, Lengauer T. 1996b. Placement of medium-sized molecular fragments into active sites of proteins. J Comput Aided Mol Des 10(1): 41-54.
20. Schmitt J, Brocca S, Schmid RD, Pleiss J. 2002. Blocking the tunnel: Engineering of Candida rugosa lipase mutants with short chain length specificity. Protein Eng 15(7): 595-601.
21. Schulz T, Pleiss J, Schmid RD. 2000. Stereoselectivity of Pseudomonas cepacia lipase toward secondary alcohols: A quantitative model. Protein Sci 9: 1053-1062.
22. Smith SW. 2009. Chiral toxicology: It's the same thing...Only different. Toxicol Sci 110(1): 4-30.