2.02012-05-31 09:56:23 -06002015-10-02 02:25:48 -0600ECMDB00060M2MDB000021Acetoacetic acidAcetoacetic acid is a member of the chemical class known as Beta Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Acetoacetic acid (also called diacetic acid) is the organic compound with the formula CH3C(O)CH2CO2H. It is the simplest beta-keto acid group and like other members of this class is unstable. (WikiPedia)β-ketobutyrateβ-ketobutyric acid3-Ketobutyrate3-Ketobutyric acid3-Oxo-butanoate3-Oxo-butanoic acid3-Oxobutanate3-Oxobutanic acid3-Oxobutanoate3-Oxobutanoic acid3-Oxobutyrate3-Oxobutyric acida-Ketobutyratea-Ketobutyric acidAcetoacetateAcetoacetic acidAlpha-KetobutyrateAlpha-Ketobutyric acidb-Ketobutyrateb-Ketobutyric acidBeta-KetobutyrateBeta-Ketobutyric acidDiacetateDiacetic acidOxobutyrateOxobutyric acidα-Ketobutyrateα-Ketobutyric acidβ-Ketobutyrateβ-Ketobutyric acidC4H6O3102.0886102.0316940583-oxobutanoic acidacetoacetic acid541-50-4CC(=O)CC(O)=OInChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)WDJHALXBUFZDSR-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-0.47logs0.37solubility2.40e+02 g/lmelting_point36.5 oClogp-0.0015pka_strongest_acidic4.02pka_strongest_basic-7.5iupac3-oxobutanoic acidaverage_mass102.0886mono_mass102.031694058smilesCC(=O)CC(O)=OformulaC4H6O3inchiInChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)inchikeyWDJHALXBUFZDSR-UHFFFAOYSA-Npolar_surface_area54.37refractivity22.54polarizability9.18rotatable_bond_count2acceptor_count3donor_count1physiological_charge-1formal_charge0Butanoate metabolismec00650Tyrosine metabolismec00350Propanoate metabolism
Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA.
Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate.
Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a
bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid.
Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA.
ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate.
Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid.
Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA.PW000940ec00640MetabolicValine, leucine and isoleucine degradationec00280Microbial metabolism in diverse environmentsec01120Two-component systemec02020Acetate metabolismThe acetate biosynthesis starts with acetyl-CoA reacting with phosphate through a phosphate acetyltransferase resulting in the release of a coenzyme A and an acetyl phosphate. The latter compound in turn reacts with ADP through an acetate kinase resulting in the release of an ATP and an acetate. The acetate reacts with ATP and coenzyme A through an acetyl-CoA synthase resulting in the release of a diphosphate, an AMP and an acetyl-CoA.
Acetyl-CoA can be biosynthesized by acetoacetate reacting with an acetyl-CoA through an acetoacetyl-CoA transferase resulting in the release of an acetate and an acetoacetyl-CoA. The acetoacetyl-CoA reacts with an acetyl-CoA acetyltransferase resulting in the release of an coenzyme A and 2 acetyl-CoAPW002090Metabolicacetoacetate degradation (to acetyl CoA)ACETOACETATE-DEG-PWYSpecdb::CMs307Specdb::CMs916Specdb::CMs920Specdb::CMs962Specdb::CMs976Specdb::CMs3045Specdb::CMs30470Specdb::CMs30977Specdb::CMs30978Specdb::CMs30979Specdb::CMs30980Specdb::CMs37272Specdb::CMs160838Specdb::CMs1049391Specdb::CMs1049393Specdb::CMs1049394Specdb::CMs1049396Specdb::CMs1049398Specdb::NmrOneD1060Specdb::NmrOneD1135Specdb::NmrOneD5492Specdb::NmrOneD5493Specdb::NmrOneD5494Specdb::NmrOneD5495Specdb::NmrOneD5496Specdb::NmrOneD5497Specdb::NmrOneD5498Specdb::NmrOneD5499Specdb::NmrOneD5500Specdb::NmrOneD5501Specdb::NmrOneD5502Specdb::NmrOneD5503Specdb::NmrOneD5504Specdb::NmrOneD5505Specdb::NmrOneD5506Specdb::NmrOneD5507Specdb::NmrOneD5508Specdb::NmrOneD5509Specdb::NmrOneD5510Specdb::NmrOneD5511Specdb::NmrOneD166432Specdb::MsMs96Specdb::MsMs97Specdb::MsMs98Specdb::MsMs182799Specdb::MsMs182800Specdb::MsMs182801Specdb::MsMs183147Specdb::MsMs183148Specdb::MsMs183149Specdb::MsMs451991Specdb::MsMs1472556Specdb::MsMs2240384Specdb::MsMs2241299Specdb::MsMs2242445Specdb::MsMs2672507Specdb::MsMs2672508Specdb::MsMs2672509Specdb::MsMs3032315Specdb::MsMs3032316Specdb::MsMs3032317Specdb::NmrTwoD1118HMDB0006094C00164153443-KETOBUTYRATELINAcetoacetic acidKeseler, I. 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Analytical Letters (1985), 18(B5), 589-92. http://hmdb.ca/system/metabolites/msds/000/000/043/original/HMDB00060.pdf?1358462250Acetate CoA-transferase subunit alphaP76458ATOD_ECOLIatoDhttp://ecmdb.ca/proteins/P76458.xmlAcetate CoA-transferase subunit betaP76459ATOA_ECOLIatoAhttp://ecmdb.ca/proteins/P76459.xmlShort-chain fatty acids transporterP76460ATOE_ECOLIatoEhttp://ecmdb.ca/proteins/P76460.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAcetoacetic acid + Acetyl-CoA > Acetoacetyl-CoA + Acetic acidR01359ACETOACETYL-COA-TRANSFER-RXNAcetoacetyl-CoA + Acetic acid <> Acetoacetic acid + Acetyl-CoAR01359Acetoacetic acid + Hydrogen ion acetone + Carbon dioxideACETOACETATE-DECARBOXYLASE-RXNAcetoacetic acid + Acetyl-CoA <> Acetoacetyl-CoA + Acetic acidACETOACETYL-COA-TRANSFER-RXNLuria-Bertani (LB) mediaShake flask36.6uMtrue9.037 oCBL21 DE3Stationary phase cultures (overnight culture)14640036000Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602.17535911