KEGG   ENZYME: 1.17.9.1
Entry
EC 1.17.9.1                 Enzyme                                 
Name
4-methylphenol dehydrogenase (hydroxylating);
pchCF (gene names);
p-cresol-(acceptor) oxidoreductase (hydroxylating);
p-cresol methylhydroxylase;
4-cresol dehydrogenase (hydroxylating)
Class
Oxidoreductases;
Acting on CH or CH2 groups;
With a copper protein as acceptor
Sysname
4-methylphenol:oxidized azurin oxidoreductase (methyl-hydroxylating)
Reaction(IUBMB)
4-methylphenol + 4 oxidized azurin + H2O = 4-hydroxybenzaldehyde + 4 reduced azurin + 4 H+ (overall reaction) [RN:R02675];
(1a) 4-methylphenol + 2 oxidized azurin + H2O = 4-hydroxybenzyl alcohol + 2 reduced azurin + 2 H+ [RN:R12133];
(1b) 4-hydroxybenzyl alcohol + 2 oxidized azurin = 4-hydroxybenzaldehyde + 2 reduced azurin + 2 H+ [RN:R12134]
Reaction(KEGG)
R02675 R12133 R12134;
(other) R11194
Substrate
4-methylphenol [CPD:C01468];
oxidized azurin [CPD:C05357];
H2O [CPD:C00001];
4-hydroxybenzyl alcohol [CPD:C17467]
Product
4-hydroxybenzaldehyde [CPD:C00633];
reduced azurin [CPD:C05358];
H+ [CPD:C00080];
4-hydroxybenzyl alcohol [CPD:C17467]
Comment
This bacterial enzyme contains a flavin (FAD) subunit and a cytochrome c subunit. The flavin subunit abstracts two hydrogen atoms from the substrate, forming a quinone methide intermediate, then hydrates the latter at the benzylic carbon with a hydroxyl group derived from water. The protons are lost to the bulk solvent, while the electrons are passed to the heme on the cytochrome subunit, and from there to azurin, a small copper-binding protein that is co-localized with the enzyme in the periplasm. The first hydroxylation forms 4-hydroxybenzyl alcohol; a second hydroxylation converts this into 4-hydroxybenzaldehyde.
History
EC 1.17.9.1 created 1983 as EC 1.17.99.1, modified 2001, modified 2011, modified 2015, transferred 2018 to EC 1.17.9.1
Pathway
ec00623  Toluene degradation
ec01100  Metabolic pathways
ec01120  Microbial metabolism in diverse environments
Orthology
K05797  4-cresol dehydrogenase (hydroxylating) flavoprotein subunit
Genes
SERMCLM71_00285
PAQUDMB82_0012910
BRBEH207_06030 EH207_06350
RBDALSL_0887 ALSL_0892
VCYIX92_07590
VCTJV59_30920
VAQFIV01_07555(pchF)
PFUWKF707C_49570
PCQPcP3B5_13510(pchF_1) PcP3B5_26440(pchF_2)
PPUTL483_22020
PDRH681_14085
PALKPSAKL28_20190 PSAKL28_31390
PSOSPOS17_3788(Neut_0635) POS17_5141(pchF)
PSETTHL1_645
PSILPMA3_18570
PUMHGP31_12055
PSHHHU773_015595
MARAD0851_03225
SWPswp_2498
CPSCPS_0526 CPS_4397
COMCMT41_15235
LSDEMK97_13360
PATPatl_1202
PSYMJ1N51_10155
AMCMADE_1013080
AMHI633_14495
AMAAamad1_13995
AMALI607_13235
AMAEI876_13620
AMAOI634_13480
AMADI636_13600
AMAII635_13970
AMACMASE_13080
AMBAMBAS45_13615
AMGAMEC673_13400
AALEP13_13170
AAUSEP12_13795
GAGGlaag_3201
GNIGNIT_2517
PMESFX988_01499
LALAT746_13270
HMIsoil367_10365
CJACJA_1090
CEGD0C16_23230
TTUTERTU_2258
KIMG3T16_04385
LCJNCTC11976_00666(pchF)
MELLIVG45_13740
MMAIsS8_0581
MEINmethR_P2652
CYQQ91_0490 Q91_0494
CZACYCME_2131 CYCME_2135
CYYCPC19_10585 CPC19_10605
NOCNoc_2406
NHLNhal_1759
NWANwat_1784
TMBThimo_2585
MPURMARPU_05365
RHHE0Z06_08875
EBSECTOBSL9_1450
HAKKO116_00403
HSXHNO51_19035
OCEGU3_14310
GBIPG2T_11235 PG2T_11275
BUGBC1001_1419
BGFBC1003_1960
BYIBYI23_B003260(pchF)
BUEBRPE67_BCDS05760(pchF)
BUQAC233_09285
BXEBxe_A2781
BXBDR64_464(pchF)
BPHBphy_1706
BGEBC1002_1210
BPXBUPH_01934
BPYBphyt_1669
BUZAYM40_08230
BFNOI25_3960(pchF)
BCAIK788_0002432
PSPWBJG93_06750
PARABTO02_13235
PARBCJU94_16775 CJU94_37945 CJU94_37970 CJU94_39130 CJU94_39155
PHSC2L64_09975
PTERC2L65_09285
PGPCUJ91_09915
PCJCUJ87_09595
PTSCUJ90_10970
PMEGFNZ07_21495
PTROG5S35_08620
PGISI6I06_05480
PACPFAZ97_08150
PEWKZJ38_09475
PDIOPDMSB3_1733(pchF)
CABASBC2_59520(pchF)
BUOBRPE64_BCDS09980
AXYAXYL_04709
AISBUW96_16125
ACHRC2U31_10740
AFQAFA_05565
AAQUD3M96_07105
OUEI6G29_08425
RHYRD110_21665
PNAPnap_3838
VEIVeis_0959
CTTCtCNB1_1149
CKEB5M06_10280
HYLLPB072_05845
HYCE5678_00620
KIAG8A07_12635
MNRACZ75_05905
MASWAM586_01835
MASSCR152_02750 CR152_23340
MASZC9I28_15230
MASYDPH57_06530
MALIEYF70_12825 EYF70_27975
MUMFCL38_04555 FCL38_21570
MFLAGO485_01200
MPLIE1742_02865 E1742_15135
MANCIV454_08835 IV454_23465
PKTAT984_08865
ATERMW290_15615
NEUNE0741
NETNeut_0635 Neut_1656
NITNAL212_2695
NCOAAW31_08160
NURATY38_06915
NMUNmul_A1475
NLCEBAPG3_008560
RBUPG1C_11260
EBAebA310 ebA3165(pchF) ebA5380
ABREpbN1_03730(cmh)
APETToN1_39370(cmh)
AZAAZKH_2917
AZIAzCIB_2865
ACOMCEW83_10340
AZDCDA09_15575
AZRCJ010_19535
TMZTmz1t_1840
THUAC731_016445
TCLTchl_1580 Tchl_1596
TAKTharo_2907 Tharo_2922
SKUSulku_2563
SULJSJPD1_1025
GMEGmet_2125(pcmI)
GEMGM21_2847
GEOGeob_0119(pcmI)
GBNGEOBRER4_30090 GEOBRER4_30100
GSUBKP001_01780 KP001_01785
DMSE8L03_03070
CCXCOCOR_00350(pchF)
SURSTAUR_5202
AGEAA314_01948
AVMJQX13_22615 JQX13_23115
CCROCMC5_053350
MRMA7982_07674
DTIDesti_5508
STARG3545_20405
NARSaro_1490 Saro_1492 Saro_1652 Saro_2876 Saro_2962 Saro_3479 Saro_3875 Saro_3879
NPPPP1Y_AT11456 PP1Y_AT15458 PP1Y_AT15495 PP1Y_AT31786 PP1Y_AT31825
NOTC7W88_02235 C7W88_07630 C7W88_19365
NORFA702_13625 FA702_15700
NOGGKE62_05195 GKE62_05215
NDRHT578_07590 HT578_07710
SSYSLG_11340 SLG_11370 SLG_27820 SLG_38080
SPHRBSY17_949
SPYGYGS_C2P0045
SBARH5V43_22205 H5V43_22225
SPHGAZE99_04610
SPHYCHN51_06845 CHN51_06865
ALBAEB_P1065 AEB_P3396
AAYWYH_02883(pchF_1) WYH_03108(pchF_2)
ERYCP97_14095 CP97_14115
AOZHUE56_06715
RRURru_A3112
RRFF11_15945
MAGQMGMAQ_0999
BDQCIK05_09530
MPHUMPHO_51090
COKCOCCU_14475(pchF)
CCYCSCMU_01910
NWLNWFMUON74_30910
RHARHA1_ro03282
ROAPd630_LPD07539
GOMD7316_03404(pchF)
SMALSMALA_8211
SSOII1A49_44795
SALSSLNWT_0108
SGUSGLAU_25455
SRNA4G23_02275(pchF)
STRDNI25_07845
SFYGFH48_00340
SGFHEP81_00149
SBYH7H31_03450
SPHVF9278_42030 F9278_42070
SGXH4W23_05070
SFBCP974_12525
SDECL3078_06210 L3078_06215 L3078_06225
MIOAOA12_16300
MAURBOH66_14985
MLVCVS47_02783(pchF)
MWAE4K62_17465
MLZF6J85_16550
CPHYB5808_01085
AUMAURMO_00038
SALDFVA74_01425
LTREVS81_09570 EVS81_09590
HEAHL652_11125 HL652_11250 HL652_11255 HL652_11275
ARLAFL94_17620
ARTPE5206_04715 E5206_18250
GLUF0M17_15860
GPRJQN66_16295 JQN66_17630
PAEYKUF55_15815
THAONI17_005915
NDANdas_1184
NOABKM31_21315 BKM31_24930
NOWGBF35_21040
NCXNocox_18200(pchF)
NGNLCN96_21805
MMARMODMU_2955(vaoA)
SACEGIY23_09415
ACTNL083_7156
MPKVL20_5235
CSNCyast_1815
CYLAA637_14685
CYJCyan7822_3696
NOPNos7524_0706
PLPPle7327_1082
STANSTA3757_22280
VBSEGM51_13795
RLCK227x_46710(pchF)
TTFTHTE_3672
MCADPan265_01410(pchF)
UAMUABAM_04360
TALBFTW19_21915
SUSAcid_2038
FLIFleli_2307
CAOCelal_4032
CBATM666_16590
NDENIDE0022(pchF)
NKFNkreftii_003316
 » show all
Reference
1  [PMID:588247]
  Authors
Hopper DJ, Taylor DG.
  Title
The purification and properties of p-cresol-(acceptor) oxidoreductase (hydroxylating), a flavocytochrome from Pseudomonas putida.
  Journal
Biochem J 167:155-62 (1977)
DOI:10.1042/bj1670155
Reference
2  [PMID:7391034]
  Authors
McIntire W, Edmondson DE, Singer TP, Hopper DJ.
  Title
8 alpha-O-Tyrosyl-FAD: a new form of covalently bound flavin from p-cresol methylhydroxylase.
  Journal
J Biol Chem 255:6553-5 (1980)
Reference
3  [PMID:3920077]
  Authors
Hopper DJ, Jones MR, Causer MJ
  Title
Periplasmic location of p-cresol methylhydroxylase in Pseudomonas putida.
  Journal
FEBS Lett 182:485-8 (1985)
DOI:10.1016/0014-5793(85)80359-8
Reference
4  [PMID:2722739]
  Authors
Bossert ID, Whited G, Gibson DT, Young LY.
  Title
Anaerobic oxidation of p-cresol mediated by a partially purified methylhydroxylase from a denitrifying bacterium.
  Journal
J Bacteriol 171:2956-62 (1989)
DOI:10.1128/JB.171.6.2956-2962.1989
Reference
5  [PMID:1697166]
  Authors
Reeve CD, Carver MA, Hopper DJ
  Title
Stereochemical aspects of the oxidation of 4-ethylphenol by the bacterial enzyme  4-ethylphenol methylenehydroxylase.
  Journal
Biochem J 269:815-9 (1990)
DOI:10.1042/bj2690815
Reference
6  [PMID:17449613]
  Authors
Peters F, Heintz D, Johannes J, van Dorsselaer A, Boll M
  Title
Genes, enzymes, and regulation of para-cresol metabolism in Geobacter metallireducens.
  Journal
J Bacteriol 189:4729-38 (2007)
DOI:10.1128/JB.00260-07
Reference
7  [PMID:18658262]
  Authors
Johannes J, Bluschke A, Jehmlich N, von Bergen M, Boll M
  Title
Purification and characterization of active-site components of the putative p-cresol methylhydroxylase membrane complex from Geobacter metallireducens.
  Journal
J Bacteriol 190:6493-500 (2008)
DOI:10.1128/JB.00790-08
Other DBs
ExplorEnz - The Enzyme Database: 1.17.9.1
IUBMB Enzyme Nomenclature: 1.17.9.1
ExPASy - ENZYME nomenclature database: 1.17.9.1
BRENDA, the Enzyme Database: 1.17.9.1
CAS: 66772-07-4

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