Protein Information

Name cytochrome P450 monooxygenases
Synonyms CYP M; CYP20A1; CYP20A1 protein; Cytochrome P450 family 20 subfamily A polypeptide 1; Cytochrome P450 monooxygenase; CYP20A1 proteins; Cytochrome P450 family 20 subfamily A polypeptide 1s; Cytochrome P450 monooxygenases

Compound Information

Name naphthalene
CAS naphthalene

Reference List

PubMed Abstract RScore(About this table)
19434406 Pecyna MJ, Ullrich R, Bittner B, Clemens A, Scheibner K, Schubert R, Hofrichter M: Molecular characterization of aromatic peroxygenase from Agrocybe aegerita. Appl Microbiol Biotechnol. 2009 Oct;84(5):885-97. Epub 2009 May 12.

Members of these extracellular biocatalysts produced by agaric basidiomycetes such as Agrocybe aegerita or Coprinellus radians catalyze reactions--for example, the peroxygenation of naphthalene, toluene, dibenzothiophene, or pyridine--which are actually attributed to cytochrome P450 monooxygenases.
31(0,1,1,1) Details
17251009 Vatsyayan P, Kumar AK, Goswami P, Goswami P: Broad substrate Cytochrome P450 monooxygenase activity in the cells of Aspergillus terreus MTCC 6324. Bioresour Technol. 2008 Jan;99(1):68-75. Epub 2007 Jan 23.

Significant CYP specific activity was also detected when naphthalene (3.80+/-0.002 U mg (-1)) was used as substrate.
2(0,0,0,2) Details
17193320 Schmidt B, Faymonville T, Gembe E, Joussen N, Schuphan I: Comparison of the biotransformation of the 14C-labelled insecticide carbaryl by non-transformed and human CYP1A1-, CYP1A2-, and CYP3A4-transgenic cell cultures of Nicotiana tabacum. Chem Biodivers. 2006 Aug;3(8):878-96.

Transgenic tobacco-cell-suspension cultures expressing separately the human cytochrome P450 monooxygenases CYP1A1, CYP1A2, and CYP3A4 were utilized to study the biotransformation of the 14C-labelled insecticide carbaryl (=naphthalen-1-yl methylcarbamate).
This consisted of naphthalene-1-ol, N-(hydroxymethyl) carbaryl, 4-hydroxycarbaryl, and 5-hydroxycarbaryl, whereas the main product in non-transformed cells was N-(hydroxymethyl) carbaryl.
1(0,0,0,1) Details
16607529 Liu L, Schmid RD, Urlacher VB: Cloning, expression, and characterization of a self-sufficient cytochrome P450 monooxygenase from Rhodococcus ruber DSM 44319. Appl Microbiol Biotechnol. 2006 Oct;72(5):876-82. Epub 2006 Apr 11.

In the presence of NADPH, the P450 monooxygenase showed hydroxylation activity towards polycyclic aromatic hydrocarbons naphthalene, indene, acenaphthene, toluene, fluorene, m-xylene, and ethyl benzene.
2(0,0,0,2) Details
17448174 Kim BS, Kim SY, Park J, Park W, Hwang KY, Yoon YJ, Oh WK, Kim BY, Ahn JS: Sequence-based screening for self-sufficient P450 monooxygenase from a metagenome library. J Appl Microbiol. 2007 May;102(5):1392-400.

AIMS: Cytochrome P450 monooxygenases (CYPs) are useful catalysts for oxidation reactions.
The heterologously expressed SYK181 showed significant hydroxylase activity towards naphthalene and phenanthrene as well as towards fatty acids.
1(0,0,0,1) Details
16628447 Hofrichter M, Ullrich R: Heme-thiolate haloperoxidases: versatile biocatalysts with biotechnological and environmental significance. Appl Microbiol Biotechnol. 2006 Jul;71(3):276-88.

Heme-thiolate haloperoxidases are undoubtedly the most versatile biocatalysts of the hemeprotein family and share catalytic properties with at least three further classes of heme-containing oxidoreductases, namely, classic plant and fungal peroxidases, cytochrome P450 monooxygenases, and catalases.
The Agrocybe aegerita peroxidase (AaP) has strong brominating as well as weak chlorinating and iodating activities, and catalyzes both benzylic and aromatic hydroxylations (e.g., of toluene and naphthalene).
1(0,0,0,1) Details