KEGG   ENZYME: 1.14.13.239Help
Entry
EC 1.14.13.239              Enzyme                                 

Name
carnitine monooxygenase;
cntAB (gene names);
yeaWX (gene names)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
L-carnitine,NAD(P)H:oxygen oxidoreductase (trimethylamine-forming)
Reaction(IUBMB)
L-carnitine + NAD(P)H + H+ + O2 = (3R)-3-hydroxy-4-oxobutanoate + trimethylamine + NAD(P)+ + H2O [RN:R11875 R11911]
Reaction(KEGG)
Substrate
L-carnitine [CPD:C00318];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(3R)-3-hydroxy-4-oxobutanoate [CPD:C21761];
trimethylamine [CPD:C00565];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
The bacterial enzyme is a complex consisting of a reductase and an oxygenase components. The reductase subunit contains a flavin and a plant-type ferredoxin [2Fe-2S] cluster, while the oxygenase subunit is a Rieske-type protein in which a [2Fe-2S] cluster is coordinated by two histidine and two cysteine residues.
History
EC 1.14.13.239 created 2017
Orthology
K22443  carnitine monooxygenase subunit
K22444  carnitine monooxygenase subunit
Genes
ECO: b1802(yeaW) b1803(yeaX)
ECJ: JW1792(yeaX) JW5294(yeaW)
ECD: ECDH10B_1940(yeaW) ECDH10B_1941(yeaX)
EBW: BWG_1615(yeaW) BWG_1616(yeaX)
ECOK: ECMDS42_1476(yeaW) ECMDS42_1477(yeaX)
ECE: Z2845(yeaW) Z2846(yeaX)
ECS: ECs2511 ECs2512
ECF: ECH74115_2528 ECH74115_2529
ETW: ECSP_2374(yeaW) ECSP_2375(yeaX)
ELX: CDCO157_2345 CDCO157_2346
EOJ: ECO26_2571(yeaW) ECO26_2572(yeaX)
EOI: ECO111_2308(yeaW) ECO111_2309(yeaX)
EOH: ECO103_1991(yeaW) ECO103_1992(yeaX)
ECOO: ECRM13514_2305(yeaW) ECRM13514_2306(yeaX)
ECOH: ECRM13516_2207(yeaW) ECRM13516_2208(yeaX)
EOK: G2583_2249(yeaW) G2583_2250(yeaX)
ECR: ECIAI1_1871(yeaW) ECIAI1_1872(yeaX)
ECK: EC55989_1975(yeaW) EC55989_1976(yeaX)
ECT: ECIAI39_1250(yeaX) ECIAI39_1251(yeaW)
EOC: CE10_2084(yeaW) CE10_2085(yeaX)
EUM: ECUMN_2094(yeaW) ECUMN_2095(yeaX)
EBR: ECB_01772(yeaW) ECB_01773(yeaX)
EKF: KO11_13700(yeaX) KO11_13705(yeaW)
ELW: ECW_m1971(yeaW) ECW_m1972(yeaX)
ELL: WFL_09685(yeaW) WFL_09690(yeaX)
ELP: P12B_c1278(yeaX) P12B_c1279(yeaW)
EBL: ECD_01772(yeaW) ECD_01773(yeaX)
EBE: B21_01760(yeaW) B21_01761(yeaX)
SFL: SF1425(yeaX)
SFX: S1540(yeaX)
SFV: SFV_1426(yeaX) SFV_1427
SFE: SFxv_1613(yeaX) SFxv_1614(yeaW)
SFT: NCTC1_01526(ophA1) NCTC1_01527(yeaW)
SSN: SSON_1358(yeaX) SSON_1359(yeaW)
SBO: SBO_1285(yeaX) SBO_1286(yeaW)
SDY: SDY_1706(yeaW) SDY_1707(yeaX)
KPR: KPR_3509(yeaW) KPR_3512(xeaX)
KPX: PMK1_03351(ophA1) PMK1_03353(cbdA_1)
KPNK: BN49_2098(xeaX) BN49_2100(yeaW)
EBT: EBL_c14120(yeaW) EBL_c14130(yeaxA)
YPK: y1695
YPH: YPC_1634
YPM: YP_2307(hmp1) YP_2308(hcaA11)
SMW: SMWW4_v1c40530(yeaW) SMWW4_v1c40550(yeaX)
XNE: XNC1_0564(yeaW) XNC1_0567(yeaX)
XNM: XNC2_0552(yeaW) XNC2_0555(yeaX)
PRG: RB151_006210(antA) RB151_006230(pobB)
PHEI: NCTC12003_00623(antA) NCTC12003_00625(ophA1)
VTA: A3368(yeaW) A3370(yeaX)
PCQ: PcP3B5_28790(antA_2) PcP3B5_38790(pobB_4) PcP3B5_38810(antA_4)
PPUN: PP4_21080(yeaX) PP4_21090(yeaW)
PKC: PKB_3451(yeax3) PKB_3452(yeaW)
PSEC: CCOS191_3070(yeaW) CCOS191_3071(yeaX)
PSET: THL1_4425
ABM: ABSDF2579
ABY: ABAYE2957
ACC: BDGL_000119(yeaW) BDGL_000121(yeaX)
REH: H16_B2129(h16_B2129) H16_B2135(h16_B2135)
VEI: Veis_3584
SIL: SPO1590
BACO: OXB_3176
 » show all
Taxonomy
Reference
1  [PMID:8000862]
  Authors
Ditullio D, Anderson D, Chen CS, Sih CJ
  Title
L-carnitine via enzyme-catalyzed oxidative kinetic resolution.
  Journal
Bioorg Med Chem 2:415-20 (1994)
DOI:10.1016/0968-0896(94)80009-X
Reference
2  [PMID:24591617]
  Authors
Zhu Y, Jameson E, Crosatti M, Schafer H, Rajakumar K, Bugg TD, Chen Y
  Title
Carnitine metabolism to trimethylamine by an unusual Rieske-type oxygenase from human microbiota.
  Journal
Proc Natl Acad Sci U S A 111:4268-73 (2014)
DOI:10.1073/pnas.1316569111
  Sequence
Reference
3  [PMID:25440057]
  Authors
Koeth RA, Levison BS, Culley MK, Buffa JA, Wang Z, Gregory JC, Org E, Wu Y, Li L, Smith JD, Tang WH, DiDonato JA, Lusis AJ, Hazen SL
  Title
gamma-Butyrobetaine is a proatherogenic intermediate in gut microbial metabolism  of L-carnitine to TMAO.
  Journal
Cell Metab 20:799-812 (2014)
DOI:10.1016/j.cmet.2014.10.006
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.239
IUBMB Enzyme Nomenclature: 1.14.13.239
ExPASy - ENZYME nomenclature database: 1.14.13.239
BRENDA, the Enzyme Database: 1.14.13.239

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