KEGG ENZYME: 1.17.9.1

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

KPAS:

LUW96_25075

SERM:

CLM71_00285

PAQU:

DMB82_0012910

BRB:	EH207_06030 EH207_06350

RBD:	ALSL_0887 ALSL_0892

VCY:	IX92_07590

VCT:	JV59_30920

VAQ:	FIV01_07555(pchF)

PFUW:

KF707C_49570

PCQ:	PcP3B5_13510(pchF_1) PcP3B5_26440(pchF_2)

PPUT:

L483_22020

PALD:

LU682_010450

PDR:	H681_14085

PALK:

PSAKL28_20190 PSAKL28_31390

PSOS:

POS17_3788(Neut_0635) POS17_5141(pchF)

PSET:

THL1_645

PSIL:

PMA3_18570

PUM:	HGP31_12055

PSHH:

HU773_015595

PHYG:

JTY93_14580

PTRL:

OU419_17560

MARA:

D0851_03225

SWP:

swp_2498

CPS:	CPS_0526 CPS_4397

COM:	CMT41_15235

LSD:	EMK97_13360

PFLI:

CTT31_22445

PMAZ:

R5H13_22485

PSYM:

J1N51_10155

AMC:	MADE_1013080

AMH:	I633_14495

AMAA:

amad1_13995

AMAL:

I607_13235

AMAE:

I876_13620

AMAO:

I634_13480

AMAD:

I636_13600

AMAI:

I635_13970

AMAC:

MASE_13080

AMB:	AMBAS45_13615

AMG:	AMEC673_13400

AAL:	EP13_13170

AAUS:

EP12_13795

GAG:	Glaag_3201

GNI:

GNIT_2517

PMES:

FX988_01499

PAT:

Patl_1202

LAL:	AT746_13270

HMI:	soil367_10365

CJA:

CJA_1090

CEG:	D0C16_23230

TTU:	TERTU_2258

KIM:	G3T16_04385

LCJ:	NCTC11976_00666(pchF)

MMEO:

OOT43_03455

MELL:

IVG45_13740

MMAI:

sS8_0581

MSZE:

MSZNOR_2507(pchF)

MEIN:

methR_P2652

CYQ:	Q91_0490 Q91_0494

CZA:	CYCME_2131 CYCME_2135

CYY:	CPC19_10585 CPC19_10605

NOC:

Noc_2406

NHL:

Nhal_1759

NWA:

Nwat_1784

TMB:	Thimo_2585

MPUR:

MARPU_05365

RHH:	E0Z06_08875

RHEI:

ATY27_04105 ATY27_12835

TWG:	Thiowin_01069(pchF)

EBS:	ECTOBSL9_1450

HAK:	KO116_00403

HSX:	HNO51_19035

OCE:

GU3_14310

GBI:	PG2T_11235 PG2T_11275

BUG:	BC1001_1419

BGF:	BC1003_1960

BYI:	BYI23_B003260(pchF)

BUE:	BRPE67_BCDS05760(pchF)

BUQ:	AC233_09285

BXE:

Bxe_A2781

BXB:	DR64_464(pchF)

BPH:

Bphy_1706

BGE:	BC1002_1210

BPX:	BUPH_01934

BPY:	Bphyt_1669

BUZ:	AYM40_08230

BFN:	OI25_3960(pchF)

BCAI:

K788_0002432

PSPW:

BJG93_06750

PARA:

BTO02_13235

PARB:

CJU94_16775 CJU94_37945 CJU94_37970 CJU94_39130 CJU94_39155

PHS:	C2L64_09975

PTER:

C2L65_09285

PGP:	CUJ91_09915

PCJ:	CUJ87_09595

PTS:	CUJ90_10970

PMEG:

FNZ07_21495

PTRO:

G5S35_08620

PGIS:

I6I06_05480

PACP:

FAZ97_08150

PEW:	KZJ38_09475

PDIO:

PDMSB3_1733(pchF)

PBRY:

NDK50_07300

PSAA:

QEN71_22985

PKF:	RW095_29525

PPAI:

E1956_09400

CABA:

SBC2_59520(pchF)

BUO:	BRPE64_BCDS09980

CABK:

NK8_38650

TVL:	FAZ95_12635

AXY:	AXYL_04709

AIS:	BUW96_16125

ACHR:

C2U31_10740

AAEG:

RA224_08885

AFQ:

AFA_05565

AAQU:

D3M96_07105

OUE:	I6G29_08425

RHY:	RD110_21665

PNA:

Pnap_3838

VEI:

Veis_0959

CTT:	CtCNB1_1149

CKE:	B5M06_10280

CRJ:	QMY55_06205

HYL:	LPB072_05845

HYC:	E5678_00620

KIA:	G8A07_12635

PKT:	AT984_08865

ATER:

MW290_15615

MNR:	ACZ75_05905

MASW:

AM586_01835

MASS:

CR152_02750 CR152_23340

MASY:

DPH57_06530

MANC:

IV454_08835 IV454_23465

MENY:

LSQ66_08895

MLIR:

LPB04_17840

MASZ:

C9I28_15230

MALI:

EYF70_12825 EYF70_27975

MUM:	FCL38_04555 FCL38_21570

MFLA:

GO485_01200

MPLI:

E1742_02865 E1742_15135

TCT:	PX653_07240

RUG:	QC826_13255

EHB:	E7V67_013070

NEU:

NE0741

NET:	Neut_0635 Neut_1656

NIT:	NAL212_2695

NCO:	AAW31_08160

NUR:	ATY38_06915

NMU:	Nmul_A1475

NLC:	EBAPG3_008560

NIZ:	NNRS527_01601

RBU:	PG1C_11260

EBA:	ebA310 ebA3165(pchF) ebA5380

ABRE:

pbN1_03730(cmh)

APET:

ToN1_39370(cmh)

AZA:

AZKH_2917

AZI:	AzCIB_2865

AZD:	CDA09_15575

AZR:	CJ010_19535

TMZ:	Tmz1t_1840

THU:	AC731_016445

THAU:

C4PIVTH_0953(pchF) C4PIVTH_1038

TCL:	Tchl_1580 Tchl_1596

TAK:	Tharo_2907 Tharo_2922

ACOM:

CEW83_10340

STAR:

G3545_20405

NAR:	Saro_1490 Saro_1492 Saro_1652 Saro_2876 Saro_2962 Saro_3479 Saro_3875 Saro_3879

NPP:	PP1Y_AT11456 PP1Y_AT15458 PP1Y_AT15495 PP1Y_AT31786 PP1Y_AT31825

NOT:	C7W88_02235 C7W88_07630 C7W88_19365

NOR:	FA702_13625 FA702_15700

NOG:	GKE62_05195 GKE62_05215

NDR:	HT578_07590 HT578_07710

NHUM:

PQ457_02810 PQ457_16355 PQ457_17925 PQ457_20745

SBIN:

SBA_ch2_6540

SSY:	SLG_11340 SLG_11370 SLG_27820 SLG_38080

SPHR:

BSY17_949

SPYG:

YGS_C2P0045

SBAR:

H5V43_22205 H5V43_22225

SPHG:

AZE99_04610

SPHY:

CHN51_06845 CHN51_06865

ACOB:

P0Y56_13005

ALB:	AEB_P1065 AEB_P3396

AAY:	WYH_02883(pchF_1) WYH_03108(pchF_2)

ERY:	CP97_14095 CP97_14115

AOZ:	HUE56_06715

RRU:

Rru_A3112

RRF:

F11_15945

MAGQ:

MGMAQ_0999

SKU:	Sulku_2563

SULJ:

SJPD1_1025

GME:	Gmet_2125(pcmI)

GEM:

GM21_2847

GEO:	Geob_0119(pcmI)

GBN:	GEOBRER4_30090 GEOBRER4_30100

GSUB:

KP001_01780 KP001_01785

DMS:	E8L03_03070

DTI:	Desti_5508

CCX:	COCOR_00350(pchF)

SUR:	STAUR_5202

AGE:	AA314_01948

AVM:	JQX13_22615 JQX13_23115

CCRO:

CMC5_053350

MRM:	A7982_07674

BDQ:	CIK05_09530

MPHU:

MPHO_51090

COK:	COCCU_14475(pchF)

CCYC:

SCMU_01910

CGF:	CGUA_09370(pchF)

NWL:	NWFMUON74_30910

NSPU:

IFM12276_24670

RHA:	RHA1_ro03282

ROA:	Pd630_LPD07539

GOM:	D7316_03404(pchF)

SMAL:

SMALA_8211

SSOI:

I1A49_44795

SALS:

SLNWT_0108

SGU:	SGLAU_25455

SRN:	A4G23_02275(pchF)

STRD:

NI25_07845

SFY:	GFH48_00340

SGF:	HEP81_00149

SBY:	H7H31_03450

SPHV:

F9278_42030 F9278_42070

SGX:	H4W23_05070

SFB:	CP974_12525

SDEC:

L3078_06210 L3078_06215 L3078_06225

SROC:

RGF97_03380

SCHG:

NRO40_12680

SINN:

ABB07_15215

STRZ:

OYE22_03320

MIO:	AOA12_16300

MAUR:

BOH66_14985

MLV:	CVS47_02783(pchF)

MWA:	E4K62_17465

MLZ:	F6J85_16550

CPHY:

B5808_01085

AUM:	AURMO_00038

SALD:

FVA74_01425

LTR:	EVS81_09570 EVS81_09590

LALL:

MUN78_14610 MUN78_14635

LRP:	MUN76_10360

HEA:	HL652_11125 HL652_11250 HL652_11255 HL652_11275

ARL:	AFL94_17620

ARTP:

E5206_04715 E5206_18250

ASUF:

MNQ99_17660

AGEG:

MUG94_13280 MUG94_16725

GLU:	F0M17_15860

GPR:	JQN66_16295 JQN66_17630

GNC:	QQS42_16520

PAEY:

KUF55_15815

THAO:

NI17_005915

NDA:

Ndas_1184

AMAZ:

LUW76_45720

NOA:	BKM31_21315 BKM31_24930

NOW:	GBF35_21040

NCX:	Nocox_18200(pchF)

NGN:	LCN96_21805

NFS:	OIE67_24840

MMAR:

MODMU_2955(vaoA)

KUT:	JJ691_43600(pchF)

SACE:

GIY23_09415

ACTN:

L083_7156

CSN:	Cyast_1815

CYL:	AA637_14685

MPK:

VL20_5235

CYJ:	Cyan7822_3696

NOP:	Nos7524_0706

PLP:	Ple7327_1082

STAN:

STA3757_22280

VBS:	EGM51_13795

RLC:	K227x_46710(pchF)

SNEP:

Enr13x_12170(pchF)

TTF:

THTE_3672

BMEI:

Spa11_33430(pchF)

MCAD:

Pan265_01410(pchF)

UAM:	UABAM_04360

TALB:

FTW19_21915

SUS:

Acid_2038

LUB:	TBR22_A12170

FLI:	Fleli_2307

CAO:	Celal_4032

CBAT:

M666_16590

NDE:	NIDE0022(pchF)

NKF:	Nkreftii_003316

LOB:	NEF87_004856

» 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

DBGET integrated database retrieval system