ExplorEnz: EC 1.14.13.239

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1.14.13.239

Accepted name:

carnitine monooxygenase

Reaction:

L-carnitine + NAD(P)H + H⁺ + O₂ = (3R)-3-hydroxy-4-oxobutanoate + trimethylamine + NAD(P)⁺ + H₂O

Glossary:

(3R)-3-hydroxy-4-oxobutanoate = L-malic semialdehyde

Other name(s):

cntAB (gene names); yeaWX (gene names)

Systematic name:

L-carnitine,NAD(P)H:oxygen oxidoreductase (trimethylamine-forming)

Comments:

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 has two domains, a Rieske-type protein in which a [2Fe-2S] cluster is coordinated by two histidine and two cysteine residues, and a domain with a catalytic mononuclear iron centre [4].

Links to other databases:

BRENDA, EXPASY, Gene, KEGG, MetaCyc, PDB

References:

1.	Ditullio, D., Anderson, D., Chen, C.S. and Sih, C.J. L-Carnitine via enzyme-catalyzed oxidative kinetic resolution. Bioorg. Med. Chem. 2 (1994) 415–420. [DOI] [PMID: 8000862]
2.	Zhu, Y., Jameson, E., Crosatti, M., Schafer, H., Rajakumar, K., Bugg, T.D. and Chen, Y. Carnitine metabolism to trimethylamine by an unusual Rieske-type oxygenase from human microbiota. Proc. Natl. Acad. Sci. USA 111 (2014) 4268–4273. [DOI] [PMID: 24591617]
3.	Koeth, R.A., Levison, B.S., Culley, M.K., Buffa, J.A., Wang, Z., Gregory, J.C., Org, E., Wu, Y., Li, L., Smith, J.D., Tang, W.H., DiDonato, J.A., Lusis, A.J. and Hazen, S.L. γ-Butyrobetaine is a proatherogenic intermediate in gut microbial metabolism of L-carnitine to TMAO. Cell Metab 20 (2014) 799–812. [DOI] [PMID: 25440057]
4.	Massmig, M., Reijerse, E., Krausze, J., Laurich, C., Lubitz, W., Jahn, D. and Moser, J. Carnitine metabolism in the human gut: characterization of the two-component carnitine monooxygenase CntAB from Acinetobacter baumannii. J. Biol. Chem. 295 (2020) 13065–13078. [DOI] [PMID: 32694223]
5.	Quareshy, M., Shanmugam, M., Townsend, E., Jameson, E., Bugg, T.DH., Cameron, A.D. and Chen, Y. Structural basis of carnitine monooxygenase CntA substrate specificity, inhibition, and intersubunit electron transfer. J. Biol. Chem. 296:100038 (2021). [DOI] [PMID: 33158989]

[EC 1.14.13.239 created 2017]