Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis.

The unique catalytic properties of oxygenases (the regio-specific and/or enantio-specific hydroxylation of non-activated carbons) are of undisputed biosynthetic value. Factors that govern the economics of their industrial use include a low k(cat), a frequently decreased k(cat) in recombinant strains, limiting oxygen transfer rates in bioreactors, product inhibition, and the demanding discovery (screening) process.

[1]  Mathys,et al.  Integrated two-liquid phase bioconversion and product-recovery processes for the oxidation of alkanes: process design and economic evaluation , 1999, Biotechnology and bioengineering.

[2]  L. Wackett.  Toluene dioxygenase from Pseudomonas putida F1. , 1990, Methods in enzymology.

[3]  I. Longmuir.  Respiration rate of bacteria as a function of oxygen concentration. , 1954, The Biochemical journal.

[4]  O. Namy,et al.  ‘ER degradation’ of a mutant yeast plasma membrane protein by the ubiquitin‐proteasome pathway , 1998, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[5]  L. Wong,et al.  Protein engineering of cytochrome p450(cam) (CYP101) for the oxidation of polycyclic aromatic hydrocarbons. , 2000, Protein engineering.

[6]  J. Andersen,et al.  Sampling P450 diversity by cloning polymerase chain reaction products obtained with degenerate primers. , 1996, Methods in enzymology.

[7]  J. Goldstein,et al.  Identification of human CYP2C19 residues that confer S-mephenytoin 4'-hydroxylation activity to CYP2C9. , 2001, Biochemistry.

[8]  B. Witholt,et al.  Molecular screening for alkane hydroxylase genes in Gram-negative and Gram-positive strains. , 1999, Environmental microbiology.

[9]  D. Morin,et al.  Metabolic capabilities of CYP2F2 with various pulmonary toxicants and its relative abundance in mouse lung subcompartments. , 2001, The Journal of pharmacology and experimental therapeutics.

[10]  B. Witholt,et al.  Expression, stability and performance of the three-component alkane mono-oxygenase of Pseudomonas oleovorans in Escherichia coli. , 2000, European journal of biochemistry.

[11]  B. Ensley,et al.  Naphthalene dioxygenase: purification and properties of a terminal oxygenase component , 1983, Journal of bacteriology.

[12]  D Mansuy,et al.  Comparison of the substrate specificities of human liver cytochrome P450s 2C9 and 2C18: application to the design of a specific substrate of CYP 2C18. , 1999, Biochemistry.

[13]  G. Goma,et al.  Mechanism of enhanced oxygen transfer in fermentation using emulsified oxygen‐vectors , 1990, Biotechnology and bioengineering.

[14]  V. de Lorenzo,et al.  Engineering of a Stable Whole-Cell Biocatalyst Capable of (S)-Styrene Oxide Formation for Continuous Two-Liquid-Phase Applications , 1999, Applied and Environmental Microbiology.

[15]  L. Newman,et al.  Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4. , 1995, Biochemistry.

[16]  C. Cerniglia,et al.  Cloning, Expression, and Characterization of the katGGene, Encoding Catalase-Peroxidase, from the Polycyclic Aromatic Hydrocarbon-Degrading Bacterium Mycobacterium sp. Strain PYR-1 , 2000, Applied and Environmental Microbiology.

[17]  D. Mansuy,et al.  Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. , 1999, Biochemistry.

[18]  T. Ost,et al.  Protein engineering of cytochromes P-450. , 2000, Biochimica et biophysica acta.

[19]  S. Hartmans,et al.  Formation and degradation of styrene oxide stereoisomers by different microorganisms. , 1994 .

[20]  Gerben J. Zylstra,et al.  Identification and Molecular Characterization of an Efflux Pump Involved in Pseudomonas putida S12 Solvent Tolerance* , 1998, The Journal of Biological Chemistry.

[21]  V. Hatzimanikatis,et al.  The AlkB monooxygenase of Pseudomonas oleovorans--synthesis, stability and level in recombinant Escherichia coli and the native host. , 1997, European journal of biochemistry.

[22]  O. Hayaishi,et al.  Protocatechuate 3,4-Dioxygenase I. CRYSTALLIZATION AND CHARACTERIZATION , 1972 .

[23]  R. G. Mathys,et al.  Developments toward large-scale bacterial bioprocesses in the presence of bulk amounts of organic solvents , 1998, Extremophiles.

[24]  R. Marchant,et al.  Lipases in racemic resolutions , 2001 .

[25]  V. Massey,et al.  The Roles of Two Amino Acid Residues in the Active Site of l-Lactate Monooxygenase , 1999, The Journal of Biological Chemistry.

[26]  J. Bolin,et al.  Steady-state Kinetic Characterization and Crystallization of a Polychlorinated Biphenyl-transforming Dioxygenase* , 2000, The Journal of Biological Chemistry.

[27]  H. Neujahr,et al.  Phenol hydroxylase from yeast. Reaction with phenol derivatives. , 1978, The Journal of biological chemistry.

[28]  Arnold L. Demain,et al.  Manual of Industrial Microbiology and Biotechnology , 1986 .

[29]  J. Falck,et al.  The Highly Stereoselective Oxidation of Polyunsaturated Fatty Acids by Cytochrome P450BM-3* , 1996, The Journal of Biological Chemistry.

[30]  B. Fox,et al.  Methane monooxygenase from Methylosinus trichosporium OB3b. Purification and properties of a three-component system with high specific activity from a type II methanotroph. , 1989, The Journal of biological chemistry.

[31]  P. Trudgill,et al.  Purification and properties of cyclopentanone oxygenase of Pseudomonas NCIB 9872. , 1976, European journal of biochemistry.

[32]  W U Primrose,et al.  A single mutation in cytochrome P450 BM3 changes substrate orientation in a catalytic intermediate and the regiospecificity of hydroxylation. , 1997, Biochemistry.

[33]  B. Witholt,et al.  Preparation of optically active N-benzyl-3-hydroxypyrrolidine by enzymatic hydroxylation , 1999 .

[34]  L. Lange,et al.  Using molecular techniques to identify new microbial biocatalysts. , 1998, Trends in biotechnology.

[35]  D. Gibson,et al.  Site-directed mutagenesis of conserved amino acids in the alpha subunit of toluene dioxygenase: potential mononuclear non-heme iron coordination sites , 1996, Journal of bacteriology.

[36]  L. Wong,et al.  Oxidation of polychlorinated benzenes by genetically engineered CYP101 (cytochrome P450(cam)). , 2001, European journal of biochemistry.

[37]  Jiujiang Yu,et al.  adhA in Aspergillus parasiticus Is Involved in Conversion of 5′-Hydroxyaverantin to Averufin , 2000, Applied and Environmental Microbiology.

[38]  J. Kealey,et al.  Characterization of the macrolide P-450 hydroxylase from Streptomyces venezuelae which converts narbomycin to picromycin. , 1998, Biochemistry.

[39]  C. C. Reddy,et al.  Purification, properties and induction of a specific benzoate-4-hydroxylase from Aspergillus niger (UBC 814). , 1975, Biochimica et biophysica acta.

[40]  M. Eppink,et al.  Purification and properties of 4-hydroxybenzoate 1-hydroxylase (decarboxylating), a novel flavin adenine dinucleotide-dependent monooxygenase from Candida parapsilosis CBS604 , 1997, Journal of bacteriology.

[41]  K. Timmis,et al.  A Novel [2Fe-2S] Ferredoxin from Pseudomonas putidamt2 Promotes the Reductive Reactivation of Catechol 2,3-Dioxygenase* , 1998, The Journal of Biological Chemistry.

[42]  N. Gorlatova,et al.  Purification, characterization, and mechanism of a flavin mononucleotide-dependent 2-nitropropane dioxygenase from Neurospora crassa. , 1998, Applied and environmental microbiology.

[43]  B. Witholt,et al.  Isolation and Characterization of thecis-trans-Unsaturated Fatty Acid Isomerase ofPseudomonas oleovorans GPo12 , 1999, Journal of bacteriology.

[44]  K. Inagaki,et al.  2-Nitropropane Dioxygenase from Hansenula mrakii: Re-characterization of the Enzyme and Oxidation of Anionic Nitroalkanes , 1984 .

[45]  J. Lipscomb,et al.  Gentisate 1,2-dioxygenase from Pseudomonas. Substrate coordination to active site Fe2+ and mechanism of turnover. , 1990, The Journal of biological chemistry.

[46]  S. Harayama,et al.  PCR isolation of catechol 2,3-dioxygenase gene fragments from environmental samples and their assembly into functional genes. , 1998, Gene.

[47]  S. Harayama,et al.  Biochemical and Molecular Characterization of 1-Hydroxy-2-naphthoate Dioxygenase from Nocardioides sp. KP7* , 1998, The Journal of Biological Chemistry.

[48]  J D Lipscomb,et al.  Large kinetic isotope effects in methane oxidation catalyzed by methane monooxygenase: evidence for C-H bond cleavage in a reaction cycle intermediate. , 1996, Biochemistry.

[49]  F. Guengerich,et al.  Kinetics of Cytochrome P450 2E1-Catalyzed Oxidation of Ethanol to Acetic Acid via Acetaldehyde* , 1999, The Journal of Biological Chemistry.

[50]  B. Ensley,et al.  Construction of Metabolic Operons Catalyzing the De Novo Biosynthesis of Indigo in Escherichia coli , 1993, Bio/Technology.

[51]  P. Trudgill,et al.  The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871. , 1976, European journal of biochemistry.

[52]  M. Wubbolts,et al.  Purification and Characterization of 2-Hydroxybiphenyl 3-Monooxygenase, a Novel NADH-dependent, FAD-containing Aromatic Hydroxylase from Pseudomonas azelaica HBP1* , 1997, The Journal of Biological Chemistry.

[53]  A. Munro,et al.  The genome sequence of Mycobacterium tuberculosis reveals cytochromes P450 as novel anti-TB drug targets , 2000 .

[54]  H. Weber,et al.  Enzymatic hydroxylation reactions. , 2000, Current opinion in biotechnology.

[55]  L. Golovleva,et al.  Purification and characterization of 6-chlorohydroxyquinol 1,2-dioxygenase from Streptomyces rochei 303: comparison with an analogous enzyme from Azotobacter sp. strain GP1 , 1995, Journal of bacteriology.

[56]  B. Witholt,et al.  Biotransformation of d-Limonene to (+)trans-Carveol by Toluene-Grown Rhodococcus opacusPWD4 Cells , 2001, Applied and Environmental Microbiology.

[57]  A. Kiener,et al.  Enzymatic Oxidation of Methyl Groups on Aromatic Heterocycles: A Versatile Method for the Preparation of Heteroaromatic Carboxylic Acids , 1992 .

[58]  M. Wubbolts,et al.  Towards a Biocatalyst for (S)-Styrene Oxide Production: Characterization of the Styrene Degradation Pathway of Pseudomonas sp. Strain VLB120 , 1998, Applied and Environmental Microbiology.

[59]  K. Inouye,et al.  Practical application of mammalian cytochrome P450. , 2000, Journal of bioscience and bioengineering.

[60]  T. Shaler,et al.  Effects of dissolved oxygen concentration on biodegradation of 2,4-dichlorophenoxyacetic acid , 1986, Applied and environmental microbiology.

[61]  B. Fox,et al.  Changes in the regiospecificity of aromatic hydroxylation produced by active site engineering in the diiron enzyme toluene 4-monooxygenase. , 1997, Biochemistry.

[62]  Peter A. Williams,et al.  Biodegradation kinetics of toluene, m-xylene, p-xylene and their intermediates through the upper TOL pathway in Pseudomonas putida (pWWO). , 1998, Microbiology.

[63]  Juan L. Ramos,et al.  Efflux Pumps Involved in Toluene Tolerance in Pseudomonas putida DOT-T1E , 1998, Journal of bacteriology.

[64]  H. Kagamiyama,et al.  Purification, subunit structure, and partial amino acid sequence of metapyrocatechase. , 1983, The Journal of biological chemistry.

[65]  N. Priestley,et al.  Purification, Properties, and Characterization of Recombinant Streptomyces sp. Strain C5 DoxA, a Cytochrome P-450 Catalyzing Multiple Steps in Doxorubicin Biosynthesis , 1999, Journal of bacteriology.

[66]  Robert Hermann,et al.  Methods for Intense Aeration, Growth, Storage, and Replication of Bacterial Strains in Microtiter Plates , 2000, Applied and Environmental Microbiology.

[67]  J. Kingma,et al.  The effect of toluene on the structure and permeability of the outer and cytoplasmic membranes of Escherichia coli. , 1978, Biochimica et biophysica acta.