Escherichia coli K-12 substr. MG1655 Compound: choline

Synonyms: (2-hydroxyethyl)trimethylammonium

Superclasses: an aminea quaternary amine

Component of: BetI-choline

Summary from MetaCyc:
Choline is a quaternary ammonium compound and a fundamental metabolite for eukaryotic organisms, forming the head group of important phospholipids such as phosphatidylcholine [Mou02].

Choline is also the precursor for the neurotransmitter acetylcholine, and serves as a precursor for the formation of the important osmoprotectant glycine betaine (see glycine betaine biosynthesis III (plants) for an example) .

Animals cannot synthesize choline, which must be consumed through the diet, making it a vitamin. It is usually grouped within the B-complex vitamins.

Most microbes are also not able to produce choline, although many have transporters for its uptake.

Chemical Formula: C5H14NO

Molecular Weight: 104.17 Daltons

Monoisotopic Molecular Weight: 104.10753907670001 Daltons

choline compound structure


InChI: InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1


Unification Links: CAS:62-49-7, CAS:123-41-1, ChEBI:15354, ChemSpider:299, DrugBank:DB00122, HMDB:HMDB00097, IAF1260:33910, KEGG:C00114, MetaboLights:MTBLC15354, PubChem:305, Wikipedia:Choline

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -49.21

Reactions known to consume the compound:

glycine betaine biosynthesis I (Gram-negative bacteria) :
choline + an oxidized unknown electron acceptor → betaine aldehyde + an reduced unknown electron acceptor

Reactions known to produce the compound:

Not in pathways:
phosphocholine[periplasm] + H2O[periplasm]choline[periplasm] + phosphate[periplasm]

In Reactions of unknown directionality:

Not in pathways:
BetI + choline = BetI-choline

In Transport reactions:
choline[periplasm] + H+[periplasm]choline[cytosol] + H+[cytosol],
choline[cytosol] + 2 H+[periplasm]choline[periplasm] + 2 H+[cytosol],
a quaternary amine[periplasm] + ATP + H2O → a quaternary amine[cytosol] + ADP + phosphate + H+

Enzymes inhibited by choline, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: betaine aldehyde dehydrogenase [Falkenberg90] Inhibitor (Mechanism unknown) of: L-proline:H+ symporter [MacMillan99], crotonobetainyl-CoA reductase [Roth94]


Falkenberg90: Falkenberg P, Strom AR (1990). "Purification and characterization of osmoregulatory betaine aldehyde dehydrogenase of Escherichia coli." Biochim Biophys Acta 1990;1034(3);253-9. PMID: 2194570

MacMillan99: MacMillan SV, Alexander DA, Culham DE, Kunte HJ, Marshall EV, Rochon D, Wood JM (1999). "The ion coupling and organic substrate specificities of osmoregulatory transporter ProP in Escherichia coli." Biochim Biophys Acta 1420(1-2);30-44. PMID: 10446288

Mou02: Mou Z, Wang X, Fu Z, Dai Y, Han C, Ouyang J, Bao F, Hu Y, Li J (2002). "Silencing of phosphoethanolamine N-methyltransferase results in temperature-sensitive male sterility and salt hypersensitivity in Arabidopsis." Plant Cell 14(9);2031-43. PMID: 12215503

Roth94: Roth S, Jung K, Jung H, Hommel RK, Kleber HP (1994). "Crotonobetaine reductase from Escherichia coli--a new inducible enzyme of anaerobic metabolization of L(-)-carnitine." Antonie Van Leeuwenhoek 1994;65(1);63-9. PMID: 8060125

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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