Oxidation of acyclic monoterpenes by P450 BM-3 monooxygenase : influence of the substrate E/Z-isomerism on enzyme chemo-and regioselectivity

[1]  T. Omura,et al.  THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. I. EVIDENCE FOR ITS HEMOPROTEIN NATURE. , 1964, The Journal of biological chemistry.

[2]  A. Fulco,et al.  ω-1, ω-2 and ω-3 Hydroxylation of long-chain fatty acids, amides and alcohols by a soluble enzyme system from Bacillus megatyerium , 1975 .

[3]  J. Sambrook,et al.  Molecular Cloning: A Laboratory Manual , 2001 .

[4]  L. Narhi,et al.  Characterization of a catalytically self-sufficient 119,000-dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium. , 1986, The Journal of biological chemistry.

[5]  L. Narhi,et al.  Identification and characterization of two functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium. , 1987, The Journal of biological chemistry.

[6]  Synthesis and Structure of the Diterpenoid Peucelinendiol , 1988 .

[7]  S. Boddupalli,et al.  Fatty acid monooxygenation by cytochrome P-450BM-3. , 1990, The Journal of biological chemistry.

[8]  E. Corey,et al.  An effective system for epoxide-initiated cation-olefin cyclization , 1991 .

[9]  R. Germani,et al.  Regioselective epoxidation of allylic alcohols with monoperoxyphthalic acid in water , 1992 .

[10]  A. Archelas,et al.  Microbiological transformations. 30. Enantioselective hydrolysis of racemic epoxides: the synthesis of enantiopure insect juvenile hormone analogs (bower's compound) , 1993 .

[11]  Rama S. Bhamidipati,et al.  Cascade cyclization : synthesis of (+)-tuberine , 1994 .

[12]  N. Mori,et al.  Synthesis of(2R, 3R)-epoxyneral, a sex pheromone of the acarid mite, Caloglyphus sp. (Astigmata: Acaridae) , 1995 .

[13]  J. Falck,et al.  An Active Site Substitution, F87V, Converts Cytochrome P450 BM-3 into a Regio- and Stereoselective (14S,15R)-Arachidonic Acid Epoxygenase* , 1997, The Journal of Biological Chemistry.

[14]  A. Ribeiro,et al.  Application of a Radical Methodology toward the Synthesis of d,l-5alpha-Pregnanes and Related Steroids: A Stereoselective Radical Cascade Approach. , 1998, The Journal of organic chemistry.

[15]  Diastereoselective Synthesis of (2S*,3R*)- and (2R*,3R*)-2,6-Dimethyl-2-homoprenylchroman-3-ol , 1998 .

[16]  MilesCS ChapmanSK LysekDA MacKayAC ReidGA HanzlikRP MunroA NobleMA.  Roles of key active-site residues in flavocytochrome P450 BM3. , 1999 .

[17]  A. Munro,et al.  Roles of key active-site residues in flavocytochrome P450 BM3. , 1999, The Biochemical journal.

[18]  U. Schwaneberg,et al.  A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes. , 2001, Journal of biotechnology.

[19]  R. Schmid,et al.  Engineering Cytochrome P450 BM-3 for Oxidation of Polycyclic Aromatic Hydrocarbons , 2001, Applied and Environmental Microbiology.

[20]  L. Wong,et al.  Protein engineering of Bacillus megaterium CYP102. The oxidation of polycyclic aromatic hydrocarbons. , 2001, European journal of biochemistry.

[21]  Frances H. Arnold,et al.  Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase , 2002, Nature Biotechnology.

[22]  K. R. Marshall,et al.  P450 BM3: the very model of a modern flavocytochrome. , 2002, Trends in biochemical sciences.

[23]  R. Croteau,et al.  Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation. , 2002, Biochemistry.

[24]  V. Urlacher,et al.  Immobilisation of P450 BM‐3 and an NADP+ Cofactor Recycling System: Towards a Technical Application of Heme‐Containing Monooxygenases in Fine Chemical Synthesis , 2003 .

[25]  Alessandro Vadalà,et al.  A Simple and Efficient Highly Enantioselective Synthesis of α-Ionone and α-Damascone , 2004 .

[26]  T. Tashiro,et al.  Enzyme-assisted synthesis of (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle, and its (R)-enantiomer , 2005 .

[27]  V. Urlacher,et al.  Catalytic Hydroxylation in Biphasic Systems using CYP102A1 Mutants , 2005 .

[28]  V. Urlacher,et al.  Altering the Regioselectivity of Cytochrome P450 CYP102A3 of Bacillus subtilis by Using a New Versatile Assay System , 2006, Chembiochem : a European journal of chemical biology.

[29]  F. Arnold,et al.  Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3. , 2006, Journal of the American Chemical Society.

[30]  F. Arnold,et al.  Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450. , 2006, Biotechnology and bioengineering.

[31]  N. Vermeulen,et al.  Heterotropic and homotropic cooperativity by a drug-metabolising mutant of cytochrome P450 BM3. , 2006, Biochemical and biophysical research communications.

[32]  V. Urlacher,et al.  Biotransformation of β-ionone by engineered cytochrome P450 BM-3 , 2006, Applied Microbiology and Biotechnology.

[33]  M. Cryle,et al.  Are branched chain fatty acids the natural substrates for P450(BM3)? , 2006, Chemical communications.

[34]  K. Lunau,et al.  Species-Specific Antennal Responses to Tibial Fragrances by Male Orchid Bees , 2006, Journal of Chemical Ecology.