PathBank

Pathway Description

Phenylethylamine Metabolism

Escherichia coli

Category:

Metabolite Pathway

Sub-Category:

Metabolic

Created: 2015-10-02

Last Updated: 2025-01-30

The process of phenylethylamine metabolism starts with 2-phenylethylamine interacting with an oxygen molecule and a water molecule in the periplasmic space through a phenylethylamine oxidase. This reaction results in the release of a hydrogen peroxide, ammonium and phenylacetaldehyde. Phenylacetaldehyde is introduced into the cytosol and degraded into phenylacetate by reaction with a phenylacetaldehyde dehydrogenase. This reaction involves phenylacetaldehyde interacting with NAD, and a water molecule and then resulting in the release of NADH, and 2 hydrogen ion. Phenylacetate is then degraded. The first step involves phenylacetate interacting with an coenzyme A and an ATP driven phenylacetate-CoA ligase resulting in the release of a AMP, a diphosphate and a phenylacetyl-CoA. This resulting compound the interacts with a hydrogen ion, NADPH, and oxygen molecule through a ring 1,2-phenylacetyl-CoA epoxidase protein complex resulting in the release of a water molecule, an NADP and a 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA. This compound is then metabolized by a ring 1,2 epoxyphenylacetyl-CoA isomerase resulting in a 2-oxepin-2(3H)-ylideneacetyl-CoA. This compound is then hydrolated through a oxepin-CoA hydrolase resulting in a 3-oxo-5,6-didehydrosuberyl-CoA semialdehyde. This commpound then interacts with a water molecule and NADP driven 3-oxo-5,6-dehydrosuberyl-CoA semialadehyde dehydrogenase resulting in 2 hydrogen ions, a NADPH and a 3-oxo-5,6-didehydrosuberyl-CoA. The resulting compound interacts with a coenzyme A and a 3-oxo-5,6 dehydrosuberyl-CoA thiolase resulting in an acetyl-CoA and a 2,3-didehydroadipyl-CoA. This resulting compound is the hydrated by a 2,3-dehydroadipyl-CoA hydratas resulting in a 3-hydroxyadipyl-CoA whuch is dehydrogenated through an NAD driven 3-hydroxyadipyl-CoA dehydrogenase resulting in a NADH, a hydrogen ion and a 3-oxoadipyl-CoA. The latter compound then interacts with conezyme A through a beta-ketoadipyl-CoA thiolase resulting in an acetyl-CoA and a succinyl-CoA. The succinyl-CoA is then integrated into the TCA cycle.

References

Phenylethylamine Metabolism References

Ferrandez A, Prieto MA, Garcia JL, Diaz E: Molecular characterization of PadA, a phenylacetaldehyde dehydrogenase from Escherichia coli. FEBS Lett. 1997 Apr 7;406(1-2):23-7.

Pubmed: 9109378

Parrott S, Jones S, Cooper RA: 2-Phenylethylamine catabolism by Escherichia coli K12. J Gen Microbiol. 1987 Feb;133(2):347-51. doi: 10.1099/00221287-133-2-347.

Pubmed: 3309152

Ravindra Kumar S, Imlay JA: How Escherichia coli tolerates profuse hydrogen peroxide formation by a catabolic pathway. J Bacteriol. 2013 Oct;195(20):4569-79. doi: 10.1128/JB.00737-13. Epub 2013 Aug 2.

Pubmed: 23913322

Parsons MR, Convery MA, Wilmot CM, Yadav KD, Blakeley V, Corner AS, Phillips SE, McPherson MJ, Knowles PF: Crystal structure of a quinoenzyme: copper amine oxidase of Escherichia coli at 2 A resolution. Structure. 1995 Nov 15;3(11):1171-84.

Pubmed: 8591028

Steinebach V, Benen JA, Bader R, Postma PW, De Vries S, Duine JA: Cloning of the maoA gene that encodes aromatic amine oxidase of Escherichia coli W3350 and characterization of the overexpressed enzyme. Eur J Biochem. 1996 May 1;237(3):584-91. doi: 10.1111/j.1432-1033.1996.0584p.x.

Pubmed: 8647101

Aiba H, Baba T, Hayashi K, Inada T, Isono K, Itoh T, Kasai H, Kashimoto K, Kimura S, Kitakawa M, Kitagawa M, Makino K, Miki T, Mizobuchi K, Mori H, Mori T, Motomura K, Nakade S, Nakamura Y, Nashimoto H, Nishio Y, Oshima T, Saito N, Sampei G, Horiuchi T, et al.: A 570-kb DNA sequence of the Escherichia coli K-12 genome corresponding to the 28.0-40.1 min region on the linkage map. DNA Res. 1996 Dec 31;3(6):363-77. doi: 10.1093/dnares/3.6.363.

Pubmed: 9097039

Hanlon SP, Hill TK, Flavell MA, Stringfellow JM, Cooper RA: 2-phenylethylamine catabolism by Escherichia coli K-12: gene organization and expression. Microbiology. 1997 Feb;143 ( Pt 2):513-8. doi: 10.1099/00221287-143-2-513.

Pubmed: 9043126

Ferrandez A, Prieto MA, Garcia JL, Diaz E: Molecular characterization of PadA, a phenylacetaldehyde dehydrogenase from Escherichia coli. FEBS Lett. 1997 Apr 7;406(1-2):23-7. doi: 10.1016/s0014-5793(97)00228-7.

Pubmed: 9109378

Ferrandez A, Minambres B, Garcia B, Olivera ER, Luengo JM, Garcia JL, Diaz E: Catabolism of phenylacetic acid in Escherichia coli. Characterization of a new aerobic hybrid pathway. J Biol Chem. 1998 Oct 2;273(40):25974-86. doi: 10.1074/jbc.273.40.25974.

Pubmed: 9748275

Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-62. doi: 10.1126/science.277.5331.1453.

Pubmed: 9278503

Hayashi K, Morooka N, Yamamoto Y, Fujita K, Isono K, Choi S, Ohtsubo E, Baba T, Wanner BL, Mori H, Horiuchi T: Highly accurate genome sequences of Escherichia coli K-12 strains MG1655 and W3110. Mol Syst Biol. 2006;2:2006.0007. doi: 10.1038/msb4100049. Epub 2006 Feb 21.

Pubmed: 16738553

This pathway was propagated using PathWhiz - Pon, A. et al. Pathways with PathWhiz (2015) Nucleic Acids Res. 43(Web Server issue): W552–W559.

Propagated from SMP0002041

	2,3-didehydroadipyl-CoA
	2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
	2-Oxepin-2(3H)-ylideneacetyl-CoA
	3-Hydroxyadipyl-CoA
	3-Oxo-5,6-dehydrosuberyl-CoA
	3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
	3-Oxoadipyl-CoA
	Acetyl-CoA
	Adenosine monophosphate
	Adenosine triphosphate
	Ammonium
	Coenzyme A
	Copper
	Hydrogen Ion
	Hydrogen peroxide
	NAD
	NADH
	NADP
	NADPH
	Oxygen
	Phenylacetaldehyde
	Phenylacetic acid
	Phenylacetyl-CoA
	Phenylethylamine
	Pyrophosphate
	Succinyl-CoA
	Topaquinone
	Water

	Beta-ketoadipyl-CoA thiolase
	Phenylacetaldehyde dehydrogenase
	Phenylacetate-coenzyme A ligase
	Phenylacetic acid degradation protein paaA
	Phenylacetic acid degradation protein paaB
	Phenylacetic acid degradation protein paaC
	Primary amine oxidase
	Probable 3-hydroxybutyryl-CoA dehydrogenase
	Probable enoyl-CoA hydratase paaF
	Probable enoyl-CoA hydratase paaG
	Probable phenylacetic acid degradation NADH oxidoreductase paaE
	Protein maoC

		2,3-didehydroadipyl-CoA
		2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
		2-Oxepin-2(3H)-ylideneacetyl-CoA
		3-Hydroxyadipyl-CoA
		3-Oxo-5,6-dehydrosuberyl-CoA
		3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
		3-Oxoadipyl-CoA
		Acetyl-CoA
		Adenosine monophosphate
		Adenosine triphosphate
		Ammonium
		Coenzyme A
		Copper
		Hydrogen Ion
		Hydrogen peroxide
		NAD
		NADH
		NADP
		NADPH
		Oxygen
		Phenylacetaldehyde
		Phenylacetic acid
		Phenylacetyl-CoA
		Phenylethylamine
		Pyrophosphate
		Succinyl-CoA
		Topaquinone
		Water

		Beta-ketoadipyl-CoA thiolase
		Phenylacetaldehyde dehydrogenase
		Phenylacetate-coenzyme A ligase
		Phenylacetic acid degradation protein paaA
		Phenylacetic acid degradation protein paaB
		Phenylacetic acid degradation protein paaC
		Primary amine oxidase
		Probable 3-hydroxybutyryl-CoA dehydrogenase
		Probable enoyl-CoA hydratase paaF
		Probable enoyl-CoA hydratase paaG
		Probable phenylacetic acid degradation NADH oxidoreductase paaE
		Protein maoC

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Phenylethylamine Metabolism

Phenylethylamine Metabolism References