Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives.
Identifieur interne : 000884 ( Main/Exploration ); précédent : 000883; suivant : 000885Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives.
Auteurs : Hiroshi Teramoto [Japon] ; Hiroo Tanaka ; Hiroyuki WariishiSource :
- FEMS microbiology letters [ 0378-1097 ] ; 2004.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Toluène.
- enzymologie : Phanerochaete.
- métabolisme : Cytochrome P-450 enzyme system, Protéines fongiques, Toluène.
- Chromatographie en phase liquide à haute performance, Hydroxylation, Spécificité du substrat.
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Toluene.
- chemical , metabolism : Cytochrome P-450 Enzyme System, Fungal Proteins, Toluene.
- enzymology : Phanerochaete.
- Chromatography, High Pressure Liquid, Hydroxylation, Substrate Specificity.
Abstract
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.
DOI: 10.1016/j.femsle.2004.03.036
PubMed: 15135530
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives.</title><author><name sortKey="Teramoto, Hiroshi" sort="Teramoto, Hiroshi" uniqKey="Teramoto H" first="Hiroshi" last="Teramoto">Hiroshi Teramoto</name><affiliation wicri:level="4"><nlm:affiliation>Faculty of Agriculture, Department of Forest and Forest Products Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Faculty of Agriculture, Department of Forest and Forest Products Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581</wicri:regionArea><orgName type="university">Université de Kyūshū</orgName><placeName><settlement type="city">Fukuoka</settlement><region type="province">Kyūshū</region><region type="prefecture">Préfecture de Fukuoka</region></placeName></affiliation></author><author><name sortKey="Tanaka, Hiroo" sort="Tanaka, Hiroo" uniqKey="Tanaka H" first="Hiroo" last="Tanaka">Hiroo Tanaka</name></author><author><name sortKey="Wariishi, Hiroyuki" sort="Wariishi, Hiroyuki" uniqKey="Wariishi H" first="Hiroyuki" last="Wariishi">Hiroyuki Wariishi</name></author></analytic><series><title level="j">FEMS microbiology letters</title><idno type="ISSN">0378-1097</idno><imprint><date when="2004" type="published">2004</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Chromatography, High Pressure Liquid (MeSH)</term><term>Cytochrome P-450 Enzyme System (metabolism)</term><term>Fungal Proteins (metabolism)</term><term>Hydroxylation (MeSH)</term><term>Phanerochaete (enzymology)</term><term>Substrate Specificity (MeSH)</term><term>Toluene (analogs & derivatives)</term><term>Toluene (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Chromatographie en phase liquide à haute performance (MeSH)</term><term>Cytochrome P-450 enzyme system (métabolisme)</term><term>Hydroxylation (MeSH)</term><term>Phanerochaete (enzymologie)</term><term>Protéines fongiques (métabolisme)</term><term>Spécificité du substrat (MeSH)</term><term>Toluène (analogues et dérivés)</term><term>Toluène (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Toluene</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Cytochrome P-450 Enzyme System</term><term>Fungal Proteins</term><term>Toluene</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Toluène</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Phanerochaete</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Phanerochaete</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Cytochrome P-450 enzyme system</term><term>Protéines fongiques</term><term>Toluène</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Chromatography, High Pressure Liquid</term><term>Hydroxylation</term><term>Substrate Specificity</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Chromatographie en phase liquide à haute performance</term><term>Hydroxylation</term><term>Spécificité du substrat</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">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.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">15135530</PMID><DateCompleted><Year>2004</Year><Month>07</Month><Day>19</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0378-1097</ISSN><JournalIssue CitedMedium="Print"><Volume>234</Volume><Issue>2</Issue><PubDate><Year>2004</Year><Month>May</Month><Day>15</Day></PubDate></JournalIssue><Title>FEMS microbiology letters</Title><ISOAbbreviation>FEMS Microbiol Lett</ISOAbbreviation></Journal><ArticleTitle>Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives.</ArticleTitle><Pagination><MedlinePgn>255-60</MedlinePgn></Pagination><Abstract><AbstractText>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. 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