Open AccessFungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives
Author(s) -
Teramoto Hiroshi,
Tanaka Hiroo,
Wariishi Hiroyuki
Publication year - 2004
Publication title -
fems microbiology letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.899
H-Index - 151
eISSN - 1574-6968
pISSN - 0378-1097
DOI - 10.1111/j.1574-6968.2004.tb09541.x
Subject(s) - hydroxylation , hydroxymethyl , cytochrome , chemistry , cytochrome p450 , stereochemistry , biochemistry , organic chemistry , enzyme
The degradation of a series of nitroaromatic compounds by the lignin‐degrading fungus Phanerochaete chrysosporium was examined. From 4‐nitrotoluene (4‐NT), several metabolic intermediates were identified. Initially, 4‐NT was converted to 4‐nitrobenzyl alcohol (4‐NBA), followed by the oxidation reactions to form 4‐nitrobenzaldehyde and 4‐nitrobenzoic acid, albeit slowly. Exogenously added 4‐nitrobenzaldehyde and 4‐nitrobenzoic acid were predominantly reduced to 4‐NBA. The fungal formation of 4‐NBA was inhibited by piperonyl butoxide, a cytochrome P450 inhibitor, suggesting the involvement of cytochrome P450 in the hydroxylation of the methyl group. Similarly, 2‐, and 3‐nitrotoluenes and 4‐chlorotoluene were converted to the corresponding arylalcohols by P. chrysosporium . On the other hand, toluene and 4‐methoxytoluene were not converted. Thus, P. chrysosporium possesses an alkyl hydroxylation activity against aromatic compounds substituted with a strong electron‐withdrawing group.