Cloning, expression and characterization of a versatile Baeyer-Villiger monooxygenase from dietzia sp. D5

AMB Express

Volumn 4, Issue 1, 2014, Pages 1-10

  Bisagni, Serena ^a   Hatti Kaul, Rajni ^a   Mamo, Gashaw ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

Baeyer villiger monooxygenase; Biocatalysis; Enzyme stability; Protein expression

Indexed keywords

BAEYER VILLIGER MONOOXYGENASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ACTINOMYCES; AFFINITY CHROMATOGRAPHY; ARTICLE; DIETZIA; ENZYME ACTIVITY; ENZYME STABILITY; ENZYME SUBSTRATE; ESCHERICHIA COLI; FREEZE THAWING; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PH; PHYLOGENETIC TREE; PHYLOGENY; POLYMERASE CHAIN REACTION; PROTEIN EXPRESSION; PROTEIN PURIFICATION; SEQUENCE ANALYSIS; SEQUENCE HOMOLOGY;

EID: 84899645132     PISSN: None     EISSN: 21910855     Source Type: Journal    
DOI: 10.1186/s13568-014-0023-1     Document Type: Article

References (36)

1. Baeyer A, Villiger V (1899) Einwirkung des caro'schen reagens auf ketone. Ber der Dtsch Chem Ges 32:3625-3633. doi:10.1002/cber.189903203151
2. Baldwin CVF, Wohlgemuth R, Woodley JM (2008) The first 200-L scale asymmetric Baeyer-Villiger oxidation using a whole-cell biocatalyst. Org Process Res and Dev 12:660-665. doi:10.1021/op800046t
3. Beneventi E, Ottolina G, Carrea G, Panzeri W, Fronza G, Lau PCK (2009) Enzymatic Baeyer-Villiger oxidation of steroids with cyclopentadecanone monooxygenase. J of Mol Catal B: Enzym 58:164-168. doi:10.1016/j.molcatb.2008.12.009
4. Bianchi DA, Moran-Ramallal R, Iqbal N, Rudroff F, Mihovilovic MD (2013) Enantiocomplementary access to carba-analogs of C-nucleoside derivatives by recombinant Baeyer-Villiger monooxygenases. Bioorg Med Chem Lett 23:2718-2720. doi:10.1016/j.bmcl.2013.02.085
5. Bisagni S, Summers B, Kara S, Hatti-Kaul R, Grogan G, Mamo G, Hollmann F (2014) Exploring the substrate specificity and enantioselectivity of a Baeyer-Villiger monooxygenase from Dietzia sp. D5: oxidation of sulfides and aldehydes. Top Catal 57:366-375. doi:10.1007/s11244-013-0192-1
6. Clouthier CM, Pelletier JN (2012) Expanding the organic toolbox: a guide to integrating biocatalysis in synthesis. Chem Soc Rev 41:1585-1605. doi:10.1039/c2cs15286j
7. de Gonzalo G, Ottolina G, Zambianchi F, Fraaije MW, Carrea G (2006) Biocatalytic properties of Baeyer-Villiger monooxygenases in aqueous-organic media. J Mol Catal B: Enzym 39:91-97. doi:10.1016/j.molcatb.2006.01.010
8. de Gonzalo G, Rodríguez C, Rioz-Martínez A, Gotor V (2012) Improvement of the biocatalytic properties of one phenylacetone monooxygenase mutant in hydrophilic organic solvents. Enzym Microb Technol 50:43-49. doi:10.1016/ j.enzmictec.2011.09.006
9. Fink MJ, Fischer TC, Rudroff F, Dudek H, Fraaije MW, Mihovilovic MD (2011) Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer-Villiger biocatalyst reveals novel regiodivergent oxidations. J Mol Catal B: Enzym 73:9-16. doi:10.1016/j.molcatb.2011.07.003
10. Fink MJ, Rial DV, Kapitanova P, Lengar A, Rehdorf J, Cheng Q, Rudroff F, Mihovilovic MD (2012) Quantitative comparison of chiral catalysts selectivity and performance: a generic concept illustrated with cyclododecanone monooxygenase as Baeyer-Villiger biocatalyst. Adv Synth Catal 354:3491-3500. doi:10.1002/adsc.201200453
11. Fraaije MW, Wu J, Heuts DPHM, van Hellemond EW, Spelberg JHL, Janssen DB (2005) Discovery of a thermostable Baeyer-Villiger monooxygenase by genome mining. Appl Microbiol Biotechnol 66:393-400. doi:10.1007/ s00253-004-1749-5
12. Griffin M, Trudgill PW (1976) Purification and properties of cyclopentanone oxygenase of Pseudomonas NCIB 9872. Eur J Biochem 63:199-209. doi:10.1111/j.1432-1033.1976.tb10222.x
13. Iwaki H, Wang S, Grosse S, Bergeron H, Nagahashi A, Lertvorachon J, Yang J, Konishi Y, Hasegawa Y, Lau PCK (2006) Pseudomonad cyclopentadecanone monooxygenase displaying an uncommon spectrum of Baeyer-Villiger oxidations of cyclic ketones. Appl Environ Microbiol 72:2707-2720. doi:10.1128/AEM.72.4.2707-2720.2006
14. Jiang J, Tetzlaff CN, Takamatsu S, Iwatsuki M, Komatsu M, Ikeda H, Cane DE (2009) Genome mining in Streptomyces avermitilis: a biochemical Baeyer-Villiger reaction and discovery of a new branch of the pentalenolactone family tree. Biochem 48:6431-6440. doi:10.1021/bi900766w
15. Kadow M, Loschinski K, Saß S, Schmidt M, Bornscheuer U (2012) Completing the series of BVMOs involved in camphor metabolism of Pseudomonas putida NCIMB 10007 by identification of the two missing genes, their functional expression in E. coli and biochemical characterization. Appl Microbiol Biotechnol 96:419-429. doi:10.1007/s00253-011-3859-1
16. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685. doi:10.1038/227680a0
17. Leisch H, Morley K, Lau PCK (2011) Baeyer-Villiger Monooxygenases: more than just green chemistry. Chem Rev 111:4165-4222. doi:10.1021/cr1003437
18. Malito E, Alfieri A, Fraaije MW, Mattevi A (2004) Crystal structure of a Baeyer-Villiger monooxygenase. Proc Natl Acad Sci USA 101:13157-13162. doi:10.1073/pnas.0404538101
19. Miyamoto M, Matsumoto J, Iwaya T, Itagaki E (1995) Bacterial steroid monooxygenase catalyzing the Baeyer-Villiger oxidation of C21-ketosteroids from Rhodococcus rhodochrous: the isolation and characterization. Biochim Biophys Acta - Prot Struct Mol Enzymol 1251:115-124. doi:10.1016/ 0167-4838(95)00090-H
20. Nam JW, Nojiri H, Noguchi H, Uchimura H, Yoshida T, Habe H, Yamane H, Omori T (2002) Purification and characterization of carbazole 1,9a-dioxygenase, a three-component dioxygenase system of Pseudomonas resinovorans strain CA10. Appl Environ Microbiol 68:5882-5890. doi:10.1128/AEM.68.12.5882-5890.2002
21. Plakunov VK, Zhurina MV, Belyaev SS (2008) Resistance of the oil-oxidizing microorganism Dietzia sp. to hyperosmotic shock in reconstituted biofilms. Microbiol 77:515-522. doi:10.1134/S0026261708050019
22. Pollard DJ, Woodley JM (2007) Biocatalysis for pharmaceutical intermediates: the future is now. Trends Biotechnol 25:66-73. doi:10.1016/j.tibtech.2006.12.005
23. Procópio L, Alvarez V, Jurelevicius D, Hansen L, Sørensen S, Cardoso J, Pádula M, Leitão Á, Seldin L, van Elsas J (2012) Insight from the draft genome of Dietzia cinnamea P4 reveals mechanisms of survival in complex tropical soil habitats and biotechnology potential. Antonie Van Leeuwenhoek 101:289-301. doi:10.1007/s10482-011-9633-7
24. Qiao K, Chooi Y-H, Tang Y (2011) Identification and engineering of the cytochalasin gene cluster from Aspergillus clavatus NRRL 1. Metab Eng 13:723-732. doi:10.1016/j.ymben.2011.09.008
25. Ramesh NP (2008) Synthesis of chiral pharmaceutical intermediates by biocatalysis. Coord Chem Rev 252:659-701. doi:10.1016/j.ccr.2007.10.031
26. Rehdorf J, Zimmer CL, Bornscheuer UT (2009) Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas putida JD1. Appl Environ Microbiol 75:3106-3114. doi:10.1128/AEM.02707-08
27. Secundo F, Fialà S, Fraaije MW, de Gonzalo G, Meli M, Zambianchi F, Ottolina G (2011) Effects of water miscible organic solvents on the activity and conformation of the Baeyer-Villiger monooxygenases from Thermobifida fusca and Acinetobacter calcoaceticus: a comparative study. Biotechnol Bioeng 108:491-499. doi:10.1002/bit.22963
28. Secundo F, Zambianchi F, Crippa G, Carrea G, Tedeschi G (2005) Comparative study of the properties of wild type and recombinant cyclohexanone monooxygenase, an enzyme of synthetic interest. J Mol Catal B: Enzym 34:1-6. doi:10.1016/j.molcatb.2005.04.001
29. Stewart JD (1998) Cyclohexanone monooxygenase: a useful asymmetric Baeyer-Villiger reactions. Curr Org Chem 2:195-216. doi:10.1002/chin.199844320
30. Trudgill PW (1990) Cyclohexanone 1,2-monooxygenase from Acinetobacter NCIMB 9871. Methods Enzymol 188:70-77. doi:10.1016/0076-6879(90)88014-2
31. Völker A, Kirschner A, Bornscheuer U, Altenbuchner J (2008) Functionalexpression, purification, and characterization of the recombinant Baeyer-Villiger monooxygenase MekA from Pseudomonas veronii MEK700. Appl Microbiol Biotechnol 77:1251-1260. doi:10.1007/s00253-007-1264-6
32. Walsh CT, Chen YCJ (1988) Enzymic Baeyer-Villiger oxidations by flavin-dependent monooxygenases. Angew Chem Int Ed 27:333-343. doi:10.1002/anie.198803331
33. Wang L, Wang W (2007) Coenzyme precursor-assisted expression of a cholesterol oxidase from Brevibacterium sp. in Escherichia coli. Biotechnol Lett 29:761-766. doi:10.1007/s10529-006-9295-0
34. Woodley JM (2013) Protein engineering of enzymes for process applications. Curr Opin Chem Biol 17:310-316. doi:10.1016/j.cbpa.2013.03.017
35. Yoshikane Y, Yokochi N, Ohnishi K, Yagia T (2004) Coenzyme precursor-assisted cooperative overexpression of an active pyridoxine 4-oxidase from Microbacterium luteolum. Prot Expr Purif 34:243-248. doi:10.1016/ j.pep.2003.11.013
36. Zambianchi F, Pasta P, Carrea G, Colonna S, Gaggero N, Woodley JM (2002) Use of isolated cyclohexanone monooxygenase from recombinant Escherichia coli as a biocatalyst for Baeyer-Villiger and sulfide oxidations. Biotechnol Bioeng 78:489-496. doi:10.1002/bit.10207