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2-Ketobutyric acid (ECMDB00005) (M2MDB000001)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 09:55:11 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:00:41 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | 2-Ketobutyric acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 2-Ketobutyric acid (alpha ketobutyric acid) is involved in the metabolism of many amino acids (glycine, cysteine, methionine, valine, leucine, serine, threonine, isoleucine). It also plays a role in propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid can be produced through the lysis of cystathionine (via cystathionine gamma lyase) leading to the production of cysteine and alpha-ketobutyric acid. It is also one of the degradation products of threonine. It can be converted to propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted to succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C4H6O3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 102.0886 Monoisotopic: 102.031694058 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | TYEYBOSBBBHJIV-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 600-18-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | (1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CCC(=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Pyrrolizidines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Pyrrolizidines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 33°C [Suante, H.; Oxidation Communications 2004, V27(2), P344-348] | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid > 2-Aceto-2-hydroxy-butyrate + Carbon dioxide L-Threonine > 2-Ketobutyric acid + Ammonium 2-Ketobutyric acid + Carbon dioxide + NADH + Hydrogen ion <> D-Erythro-3-Methylmalate + NAD L-Threonine <> 2-Ketobutyric acid + Ammonia O-Succinyl-L-homoserine + Water <> 2-Ketobutyric acid + Succinic acid + Ammonia 2-Ketobutyric acid + 2-(a-Hydroxyethyl)thiamine diphosphate <> 2-Aceto-2-hydroxy-butyrate + Thiamine pyrophosphate 2-Ketobutyric acid + Coenzyme A <> Propionyl-CoA + Formic acid Pyruvic acid + 2-Ketobutyric acid <> 2-Aceto-2-hydroxy-butyrate + Carbon dioxide 2-Ketobutyric acid + Coenzyme A > Propionyl-CoA + Formic acid Hydrogen ion + 2-Ketobutyric acid + Succinic acid + Ammonia O-Succinyl-L-homoserine + Water an aminated amine donor + 2-Ketobutyric acid + Hydrogen ion 2-aminobutyrate + a deaminated amine donor L-Threonine > Hydrogen ion + 2-Ketobutyric acid + Ammonia L-Threonine > 2-Ketobutyric acid + Ammonia Iminobutyrate + Water > 2-Ketobutyric acid + Ammonia Propionyl-CoA + Formic acid > CoA + 2-Ketobutyric acid L-Threonine + 2-Aminobut-2-enoate + 2-Iminobutanoate + Water <> 2-Ketobutyric acid + Ammonia 2-Ketobutyric acid + Coenzyme A > Formic acid + Propionyl-CoA + Propionyl-CoA 2 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid >2 2-Aceto-2-hydroxy-butyrate + Carbon dioxide 2 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid >2 2-Aceto-2-hydroxy-butyrate + Carbon dioxide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Figge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl. (2006), 31pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in magnesium ion binding
- Specific function:
- 2 pyruvate = 2-acetolactate + CO(2)
- Gene Name:
- ilvI
- Uniprot ID:
- P00893
- Molecular weight:
- 62984
Reactions
2 pyruvate = 2-acetolactate + CO(2). |
- General function:
- Involved in acetolactate synthase activity
- Specific function:
- 2 pyruvate = 2-acetolactate + CO(2)
- Gene Name:
- ilvH
- Uniprot ID:
- P00894
- Molecular weight:
- 17977
Reactions
2 pyruvate = 2-acetolactate + CO(2). |
- General function:
- Involved in pyridoxal phosphate binding
- Specific function:
- O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
- Gene Name:
- metB
- Uniprot ID:
- P00935
- Molecular weight:
- 41550
Reactions
O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the formation of alpha-ketobutyrate from threonine in a two-step reaction. The first step is a dehydration of threonine, followed by rehydration and liberation of ammonia. Deaminates L-threonine, but also L-serine to a lesser extent
- Gene Name:
- ilvA
- Uniprot ID:
- P04968
- Molecular weight:
- 56195
Reactions
L-threonine = 2-oxobutanoate + NH(3). |
- General function:
- Involved in magnesium ion binding
- Specific function:
- 2 pyruvate = 2-acetolactate + CO(2)
- Gene Name:
- ilvB
- Uniprot ID:
- P08142
- Molecular weight:
- 60440
Reactions
2 pyruvate = 2-acetolactate + CO(2). |
- General function:
- Involved in transferase activity
- Specific function:
- L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine
- Gene Name:
- avtA
- Uniprot ID:
- P09053
- Molecular weight:
- 46711
Reactions
L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine. |
- General function:
- Involved in formate C-acetyltransferase activity
- Specific function:
- Acetyl-CoA + formate = CoA + pyruvate
- Gene Name:
- pflB
- Uniprot ID:
- P09373
- Molecular weight:
- 85357
Reactions
Acetyl-CoA + formate = CoA + pyruvate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Activation of pyruvate formate-lyase 1 under anaerobic conditions by generation of an organic free radical, using S- adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
- Gene Name:
- pflA
- Uniprot ID:
- P0A9N4
- Molecular weight:
- 28204
Reactions
S-adenosyl-L-methionine + dihydroflavodoxin + [formate C-acetyltransferase]-glycine = 5'-deoxyadenosine + L-methionine + flavodoxin semiquinone + [formate C-acetyltransferase]-glycin-2-yl radical. |
- General function:
- Involved in amino acid binding
- Specific function:
- 2 pyruvate = 2-acetolactate + CO(2)
- Gene Name:
- ilvN
- Uniprot ID:
- P0ADF8
- Molecular weight:
- 11106
Reactions
2 pyruvate = 2-acetolactate + CO(2). |
- General function:
- Involved in acetolactate synthase activity
- Specific function:
- 2 pyruvate = 2-acetolactate + CO(2)
- Gene Name:
- ilvM
- Uniprot ID:
- P0ADG1
- Molecular weight:
- 9703
Reactions
2 pyruvate = 2-acetolactate + CO(2). |
- General function:
- Involved in catalytic activity
- Specific function:
- Acts on both serine and threonine, and properly considered as a hydroxy amino acid deaminase
- Gene Name:
- tdcB
- Uniprot ID:
- P0AGF6
- Molecular weight:
- 35232
Reactions
L-threonine = 2-oxobutanoate + NH(3). |
L-serine = pyruvate + NH(3). |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the oxidation of 3-carboxy-2-hydroxy-4- methylpentanoate (3-isopropylmalate) to 3-carboxy-4-methyl-2- oxopentanoate. The product decarboxylates to 4-methyl-2 oxopentanoate
- Gene Name:
- leuB
- Uniprot ID:
- P30125
- Molecular weight:
- 39517
Reactions
(2R,3S)-3-isopropylmalate + NAD(+) = 4-methyl-2-oxopentanoate + CO(2) + NADH. |
- General function:
- Involved in catalytic activity
- Specific function:
- Acetyl-CoA + formate = CoA + pyruvate
- Gene Name:
- pflD
- Uniprot ID:
- P32674
- Molecular weight:
- 85959
Reactions
Acetyl-CoA + formate = CoA + pyruvate. |
- General function:
- Involved in formate C-acetyltransferase activity
- Specific function:
- Specific function unknown
- Gene Name:
- tdcE
- Uniprot ID:
- P42632
- Molecular weight:
- 85935
Reactions
Propionyl-CoA + formate = CoA + 2-oxobutanoate. |
Acetyl-CoA + formate = CoA + pyruvate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Acetyl-CoA + formate = CoA + pyruvate
- Gene Name:
- ybiW
- Uniprot ID:
- P75793
- Molecular weight:
- 90125
Reactions
Acetyl-CoA + formate = CoA + pyruvate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Acts as a radical domain for damaged PFL and possibly other radical proteins
- Gene Name:
- grcA
- Uniprot ID:
- P68066
- Molecular weight:
- 14284
- General function:
- Translation, ribosomal structure and biogenesis
- Specific function:
- May have a phosphotransferase activity
- Gene Name:
- yjgF
- Uniprot ID:
- P0AF93
- Molecular weight:
- 13612
Reactions
Iminobutyrate + H(2)O = 2-oxobutanoate + NH(3). |