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Volumn 11, Issue 7, 2016, Pages

Structural and catalytic characterization of a fungal baeyer-villiger monooxygenase

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE MONOOXYGENASE; PHENYLACETONE MONOOXYGENASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; 1-PHENYL-2-PROPANONE; ACETONE; MIXED FUNCTION OXIDASE;

EID: 85015822406     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0160186     Document Type: Article
Times cited : (34)

References (37)
  • 1
    • 0242526082 scopus 로고    scopus 로고
    • Baeyer-villiger monooxygenases an emerging family of flavin-dependent biocatalysts
    • Kamerbeek NM, Janssen DB, van Berkel WJH, Fraaije MW. Baeyer-Villiger Monooxygenases, an Emerging Family of Flavin-Dependent Biocatalysts. Adv Synth Catal. 2003; 345: 667-678. doi: 10.1002/adsc.200303014
    • (2003) Adv Synth Catal , vol.345 , pp. 667-678
    • Kamerbeek, N.M.1    Janssen, D.B.2    Van Berkel, W.J.H.3    Fraaije, M.W.4
  • 2
    • 84863953159 scopus 로고    scopus 로고
    • Discovery, application and protein engineering of baeyer-villiger monooxygenases for organic synthesis
    • PMID: 22733152
    • Balke K, Kadow M, Mallin H, Sa S, Bornscheuer UT. Discovery, application and protein engineering of Baeyer-Villiger monooxygenases for organic synthesis. Org Biomol Chem. 2012; 10: 6249-6265. doi: 10.1039/c2ob25704a PMID: 22733152
    • (2012) Org Biomol Chem , vol.10 , pp. 6249-6265
    • Balke, K.1    Kadow, M.2    Mallin, H.3    Sa, S.4    Bornscheuer, U.T.5
  • 3
    • 79960605776 scopus 로고    scopus 로고
    • Baeyer-villiger monooxygenases: More than just green chemistry
    • PMID: 21542563
    • Leisch H, Morley K, Lau PCK. Baeyer-Villiger monooxygenases: more than just green chemistry. Chem Rev. 2011; 111: 4165-4222. doi: 10.1021/cr1003437 PMID: 21542563
    • (2011) Chem Rev , vol.111 , pp. 4165-4222
    • Leisch, H.1    Morley, K.2    Lau, P.C.K.3
  • 4
    • 77949897676 scopus 로고    scopus 로고
    • Baeyer-villiger monooxygenases: Recent advances and future challenges
    • PMID: 20015679
    • Torres Pazmiño DE, Dudek HM, Fraaije MW. Baeyer-Villiger monooxygenases: recent advances and future challenges. Curr Opin Chem Biol. 2010; 14: 138-144. doi: 10.1016/j.cbpa.2009.11.017 PMID: 20015679
    • (2010) Curr Opin Chem Biol , vol.14 , pp. 138-144
    • Torres Pazmiño, D.E.1    Dudek, H.M.2    Fraaije, M.W.3
  • 5
    • 84864621472 scopus 로고    scopus 로고
    • Protein engineering of stereoselective baeyer-villiger monooxygenases
    • PMID: 22807240
    • Zhang Z-G, Parra LP, Reetz MT. Protein engineering of stereoselective Baeyer-Villiger monooxygenases. Chemistry. 2012; 18: 10160-10172. doi: 10.1002/chem.201202163 PMID: 22807240
    • (2012) Chemistry , vol.18 , pp. 10160-10172
    • Zhang, Z.-G.1    Parra, L.P.2    Reetz, M.T.3
  • 6
    • 33750451635 scopus 로고    scopus 로고
    • Designing new baeyer-villiger monooxygenases using restricted casting
    • PMID: 17064016
    • Clouthier CM, Kayser MM, Reetz MT. Designing new Baeyer-Villiger monooxygenases using restricted CASTing. J Org Chem. 2006; 71: 8431-8437. doi: 10.1021/jo0613636 PMID: 17064016
    • (2006) J Org Chem , vol.71 , pp. 8431-8437
    • Clouthier, C.M.1    Kayser, M.M.2    Reetz, M.T.3
  • 7
    • 84902485168 scopus 로고    scopus 로고
    • Functional divergence between closely related baeyer-villiger monooxygenases from aspergillus flavus
    • Ferroni FM, Smit MS, Opperman DJ. Functional divergence between closely related Baeyer-Villiger monooxygenases from Aspergillus flavus. J Mol Catal B Enzym. 2014; 107: 47-54. doi: 10.1016/j.molcatb.2014.05.015
    • (2014) J Mol Catal B Enzym , vol.107 , pp. 47-54
    • Ferroni, F.M.1    Smit, M.S.2    Opperman, D.J.3
  • 8
    • 84881227846 scopus 로고    scopus 로고
    • Cloning, overexpression and biocatalytic exploration of a novel baeyer-villiger monooxygenase from aspergillus fumigatus af293
    • PMID: 23767684
    • Mascotti ML, Juri Ayub M, Dudek H, Sanz MK, Fraaije MW. Cloning, overexpression and biocatalytic exploration of a novel Baeyer-Villiger monooxygenase from Aspergillus fumigatus Af293. AMB Express. 2013; 3: 33. doi: 10.1186/2191-0855-3-33 PMID: 23767684
    • (2013) AMB Express , vol.3 , pp. 33
    • Mascotti, M.L.1    Juri Ayub, M.2    Dudek, H.3    Sanz, M.K.4    Fraaije, M.W.5
  • 9
    • 84941309176 scopus 로고    scopus 로고
    • The origin and evolution of baeyer-villiger monooxygenases (bvmos): An ancestral family of flavin monooxygenases
    • PMID 26161776
    • Mascotti ML, Lapadula WJ, Juri Ayub M. The origin and evolution of Baeyer-Villiger monooxygenases (BVMOs): An ancestral family of flavin monooxygenases. PLoS One. 2015; 10: e0132689. doi: 10.1371/journal.pone.0132689 PMID: 26161776
    • (2015) PLoS One , vol.10 , pp. e0132689
    • Mascotti, M.L.1    Lapadula, W.J.2    Juri Ayub, M.3
  • 10
    • 4444307667 scopus 로고    scopus 로고
    • Crystal structure of a baeyer-villiger monooxygenase
    • PMID: 15328411
    • Malito E, Alfieri A, Fraaije MW, Mattevi A. Crystal structure of a Baeyer-Villiger monooxygenase. Proc Natl Acad Sci U S A. 2004; 101: 13157-13162. doi: 10.1073/pnas.0404538101 PMID: 15328411
    • (2004) Proc Natl Acad Sci U S A , vol.101 , pp. 13157-13162
    • Malito, E.1    Alfieri, A.2    Fraaije, M.W.3    Mattevi, A.4
  • 11
    • 67649607265 scopus 로고    scopus 로고
    • Crystal structures of cyclohexanone monooxygenase reveal complex domain movements and a sliding cofactor
    • PMID: 19385644
    • Mirza IA, Yachnin BJ, Wang S, Grosse S, Bergeron H, Imura A, et al. Crystal structures of cyclohexanone monooxygenase reveal complex domain movements and a sliding cofactor. J Am Chem Soc. 2009; 131: 8848-8854. doi: 10.1021/ja9010578 PMID: 19385644
    • (2009) J Am Chem Soc , vol.131 , pp. 8848-8854
    • Mirza, I.A.1    Yachnin, B.J.2    Wang, S.3    Grosse, S.4    Bergeron, H.5    Imura, A.6
  • 12
    • 84863313527 scopus 로고    scopus 로고
    • Exploring the structural basis of substrate preferences in baeyer-villiger monooxygenases: Insight from steroid monooxygenase
    • PMID: 22605340
    • Franceschini S, van Beek HL, Pennetta A, Martinoli C, Fraaije MW, Mattevi A. Exploring the structural basis of substrate preferences in Baeyer-Villiger monooxygenases: insight from steroid monooxygenase. J Biol Chem. 2012; 287: 22626-22634. doi: 10.1074/jbc.M112.372177 PMID: 22605340
    • (2012) J Biol Chem , vol.287 , pp. 22626-22634
    • Franceschini, S.1    Van Beek, H.L.2    Pennetta, A.3    Martinoli, C.4    Fraaije, M.W.5    Mattevi, A.6
  • 13
    • 84860861683 scopus 로고    scopus 로고
    • Cloning baeyer-villiger biooxidations and structures of the camphor pathway 2-oxo-?(3)-4 5,5-trimethylcyclopentenylacetyl-coenzyme a monooxygenase of pseudomonas putida atcc 17453
    • PMID: 22267661
    • Leisch H, Shi R, Grosse S, Morley K, Bergeron H, Cygler M, et al. Cloning, Baeyer-Villiger biooxidations, and structures of the camphor pathway 2-oxo-?(3)-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase of Pseudomonas putida ATCC 17453. Appl Environ Microbiol. 2012; 78: 2200-2212. doi: 10.1128/AEM.07694-11 PMID: 22267661
    • (2012) Appl Environ Microbiol , Issue.78 , pp. 2200-2212
    • Leisch, H.1    Shi, R.2    Grosse, S.3    Morley, K.4    Bergeron, H.5    Cygler, M.6
  • 14
    • 80051703580 scopus 로고    scopus 로고
    • Snapshots of enzymatic baeyer-villiger catalysis: Oxygen activation and intermediate stabilization
    • PMID: 21697090
    • Orru R, Dudek HM, Martinoli C, Torres Pazmino DE, Royant A, Weik M, et al. Snapshots of enzymatic Baeyer-Villiger catalysis: oxygen activation and intermediate stabilization. J Biol Chem. 2011; 286: 29284-29291. doi: 10.1074/jbc.M111.255075 PMID: 21697090
    • (2011) J Biol Chem , vol.286 , pp. 29284-29291
    • Orru, R.1    Dudek, H.M.2    Martinoli, C.3    Torres Pazmino, D.E.4    Royant, A.5    Weik, M.6
  • 15
    • 84860849697 scopus 로고    scopus 로고
    • The substrate-bound crystal structure of a baeyer-villiger monooxygenase exhibits a criegee-like conformation
    • PMID: 22506764
    • Yachnin BJ, Sprules T, McEvoy MB, Lau PCK, Berghuis AM. The substrate-bound crystal structure of a Baeyer-Villiger monooxygenase exhibits a Criegee-like conformation. J Am Chem Soc. 2012; 134: 7788-7795. doi: 10.1021/ja211876p PMID: 22506764
    • (2012) J Am Chem Soc , vol.134 , pp. 7788-7795
    • Yachnin, B.J.1    Sprules, T.2    McEvoy, M.B.3    Lau, P.C.K.4    Berghuis, A.M.5
  • 16
    • 84919668855 scopus 로고    scopus 로고
    • Lactone-bound structures of cyclohexanone monooxygenase provide insight into the stereochemistry of catalysis
    • PMID: 25265531
    • Yachnin BJ, McEvoy MB, MacCuish RJD, Morley KL, Lau PCK, Berghuis AM. Lactone-bound structures of cyclohexanone monooxygenase provide insight into the stereochemistry of catalysis. ACS Chem Biol. 2014; 9: 2843-2851. doi: 10.1021/cb500442e PMID: 25265531
    • (2014) ACS Chem Biol , vol.9 , pp. 2843-2851
    • Yachnin, B.J.1    McEvoy, M.B.2    MacCuish, R.J.D.3    Morley, K.L.4    Lau, P.C.K.5    Berghuis, A.M.6
  • 18
    • 0029144515 scopus 로고
    • Bacterial steroid monooxygenase catalyzing the baeyer-villiger oxidation of c21-ketosteroids from rhodococcus rhodochrous: The isolation and characterization
    • Available PMID: 7669800
    • Miyamoto M, Matsumoto J, Iwaya T, Itagaki E. Bacterial steroid monooxygenase catalyzing the Baeyer-Villiger oxidation of C21-ketosteroids from Rhodococcus rhodochrous: the isolation and characterization. Biochim Biophys Acta. 1995; 1251: 115-124. Available: http://www.ncbi.nlm.nih.gov/pubmed/7669800 PMID: 7669800
    • (1995) Biochim Biophys Acta , vol.1251 , pp. 115-124
    • Miyamoto, M.1    Matsumoto, J.2    Iwaya, T.3    Itagaki, E.4
  • 19
    • 78650008114 scopus 로고    scopus 로고
    • Towards practical baeyer-villiger-monooxygenases: Design of cyclohexanone monooxygenase mutants with enhanced oxidative stability
    • PMID: 21080396
    • Opperman DJ, Reetz MT. Towards practical Baeyer-Villiger-monooxygenases: design of cyclohexanone monooxygenase mutants with enhanced oxidative stability. Chembiochem. 2010; 11: 2589-2596. doi: 10.1002/cbic.201000464 PMID: 21080396
    • (2010) Chembiochem , vol.11 , pp. 2589-2596
    • Opperman, D.J.1    Reetz, M.T.2
  • 20
    • 14844294424 scopus 로고    scopus 로고
    • Protein production by auto-induction in high-density shaking cultures
    • PMID: 15915565
    • Studier FW. Protein production by auto-induction in high-density shaking cultures. Protein Expr Purif. 2005; 41: 207-234. doi: 10.1016/j.pep.2005.01.016 PMID: 15915565
    • (2005) Protein Expr Purif , vol.41 , pp. 207-234
    • Studier, F.W.1
  • 27
    • 84907202816 scopus 로고    scopus 로고
    • Cloning and expression of a baeyer-villiger monooxygenase oxidizing linear aliphatic ketones from dietzia sp. D5
    • Bisagni S, Smus J, Chávez G, Hatti-Kaul R, Mamo G. Cloning and expression of a Baeyer-Villiger monooxygenase oxidizing linear aliphatic ketones from Dietzia sp. D5. J Mol Catal B Enzym. 2014; 109: 161-169. doi: 10.1016/j.molcatb.2014.08.020
    • (2014) J Mol Catal B Enzym , vol.109 , pp. 161-169
    • Bisagni, S.1    Smus, J.2    Chávez, G.3    Hatti-Kaul, R.4    Mamo, G.5
  • 28
    • 84899956948 scopus 로고    scopus 로고
    • Extending the substrate scope of a baeyer-villiger monooxygenase by multiple-site mutagenesis
    • PMID: 24247989
    • Dudek HM, Fink MJ, Shivange AV, Dennig A, Mihovilovic MD, Schwaneberg U, et al. Extending the substrate scope of a Baeyer-Villiger monooxygenase by multiple-site mutagenesis. Appl Microbiol Biotechnol. 2014; 98: 4009-4020. doi: 10.1007/s00253-013-5364-1 PMID: 24247989
    • (2014) Appl Microbiol Biotechnol , vol.98 , pp. 4009-4020
    • Dudek, H.M.1    Fink, M.J.2    Shivange, A.V.3    Dennig, A.4    Mihovilovic, M.D.5    Schwaneberg, U.6
  • 29
    • 34547630476 scopus 로고    scopus 로고
    • Cloning, expression and characterization of a baeyer-villiger monooxygenase from pseudomonas putida kt2440
    • PMID 17530181
    • Rehdorf J, Kirschner A, Bornscheuer UT. Cloning, expression and characterization of a Baeyer-Villiger monooxygenase from Pseudomonas putida KT2440. Biotechnol Lett. 2007; 29: 1393-1398. doi: 10.1007/s10529-007-9401-y PMID: 17530181
    • (2007) Biotechnol Lett , vol.29 , pp. 1393-1398
    • Rehdorf, J.1    Kirschner, A.2    Bornscheuer, U.T.3
  • 30
    • 38049187059 scopus 로고    scopus 로고
    • Functional expression, purification, and characterization of the recombinant baeyer-villiger monooxygenase meka from pseudomonas veronii mek700
    • PMID: 18034235
    • Völker A, Kirschner A, Bornscheuer UT, Altenbuchner J. Functional expression, purification, and characterization of the recombinant Baeyer-Villiger monooxygenase MekA from Pseudomonas veronii MEK700. Appl Microbiol Biotechnol. 2008; 77: 1251-1260. doi: 10.1007/s00253-007-1264-6 PMID: 18034235
    • (2008) Appl Microbiol Biotechnol , vol.77 , pp. 1251-1260
    • Völker, A.1    Kirschner, A.2    Bornscheuer, U.T.3    Altenbuchner, J.4
  • 31
    • 20544473768 scopus 로고    scopus 로고
    • Enzymatic baeyer-villiger oxidation of benzaldehydes
    • Moonen MJH, Westphal AH, Rietjens IMCM, Van Berkel WJH. Enzymatic Baeyer-Villiger oxidation of benzaldehydes. Adv Synth Catal. 2005; 347: 1027-1034. doi: 10.1002/adsc.200404307
    • (2005) Adv Synth Catal , vol.347 , pp. 1027-1034
    • Moonen, M.J.H.1    Westphal, A.H.2    Imcm, R.3    Van Berkel, W.J.H.4
  • 32
    • 84871847408 scopus 로고    scopus 로고
    • Engineering of recombinant e. Coli cells co-expressing p450pyrtm monooxygenase and glucose dehydrogenase for highly regio-And stereoselective hydroxylation of alicycles with cofactor recycling
    • PMID: 22886996
    • Pham SQ, Gao P, Li Z. Engineering of recombinant E. coli cells co-expressing P450pyrTM monooxygenase and glucose dehydrogenase for highly regio-And stereoselective hydroxylation of alicycles with cofactor recycling. Biotechnol Bioeng. 2013; 110: 363-373. doi: 10.1002/bit.24632 PMID: 22886996
    • (2013) Biotechnol Bioeng , vol.110 , pp. 363-373
    • Pham, S.Q.1    Gao, P.2    Li, Z.3
  • 33
    • 0034857466 scopus 로고    scopus 로고
    • 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds
    • PMID: 11322873
    • Kamerbeek NM, Moonen MJ, Van Der Ven JG, Van Berkel WJ, Fraaije MW, Janssen DB. 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds. Eur J Biochem. 2001; 268: 2547-2557. doi: 10.1046/j.1432-1327.2001.02137.x PMID: 11322873
    • (2001) Eur J Biochem , vol.268 , pp. 2547-2557
    • Kamerbeek, N.M.1    Moonen, M.J.2    Van Der Ven, J.G.3    Van Berkel, W.J.4    Fraaije, M.W.5    Janssen, D.B.6
  • 34
    • 0037224946 scopus 로고    scopus 로고
    • Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase
    • PMID: 12514023
    • Kamerbeek NM, Olsthoorn AJJ, Fraaije MW, Janssen DB. Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase. Appl Environ Microbiol. 2003; 69: 419-426. doi: 10.1128/AEM.69.1.419 PMID: 12514023
    • (2003) Appl Environ Microbiol , vol.69 , pp. 419-426
    • Kamerbeek, N.M.1    Olsthoorn, A.J.J.2    Fraaije, M.W.3    Janssen, D.B.4
  • 35
    • 66249142686 scopus 로고    scopus 로고
    • Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from pseudomonas putida jd1
    • PMID: 19251889
    • Rehdorf J, Zimmer CL, Bornscheuer UT. Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas putida JD1. Appl Environ Microbiol. 2009; 75: 3106-3114. doi: 10.1128/AEM.02707-08 PMID: 19251889
    • (2009) Appl Environ Microbiol , vol.75 , pp. 3106-3114
    • Rehdorf, J.1    Zimmer, C.L.2    Bornscheuer, U.T.3
  • 36
    • 0037042197 scopus 로고    scopus 로고
    • Identification of a baeyer-villiger monooxygenase sequence motif
    • PMID: 11997015
    • Fraaije MW, Kamerbeek NM, van Berkel WJH, Janssen DB. Identification of a Baeyer-Villiger monooxygenase sequence motif. FEBS Lett. 2002; 518: 43-47. doi: 10.1016/S0014-5793(02)02623-6 PMID: 11997015
    • (2002) FEBS Lett , vol.518 , pp. 43-47
    • Fraaije, M.W.1    Kamerbeek, N.M.2    Van Berkel, W.J.H.3    Janssen, D.B.4
  • 37
    • 20544433645 scopus 로고    scopus 로고
    • Converting phenylacetone monooxygenase into phenylcyclohexanone monooxygenase by rational design: Towards practical baeyer-villiger monooxygenases
    • Bocola M, Schulz F, Leca F, Vogel A, Fraaije MW, Reetz MT. Converting Phenylacetone Monooxygenase into Phenylcyclohexanone Monooxygenase by Rational Design: Towards Practical Baeyer-Villiger Monooxygenases. Adv Synth Catal. 2005; 347: 979-986. doi: 10.1002/adsc.200505069
    • (2005) Adv Synth Catal , vol.347 , pp. 979-986
    • Bocola, M.1    Schulz, F.2    Leca, F.3    Vogel, A.4    Fraaije, M.W.5    Reetz, M.T.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.