Pyruvaldehyde (ECMDB01167) (M2MDB000281)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:46:43 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:10 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Pyruvaldehyde | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C3H4O2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 72.0627 Monoisotopic: 72.021129372 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | AIJULSRZWUXGPQ-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 78-98-8 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 2-oxopropanal | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | methylglyoxal | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CC(=O)C=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as alpha ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbonyl compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Alpha ketoaldehydes | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Liquid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | < 25 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Hydrogen ion + Pyruvaldehyde + NADPH > Acetol + NADP Dihydroxyacetone phosphate <> Pyruvaldehyde + Phosphate Glutathione + Pyruvaldehyde <> S-Lactoylglutathione Hydrogen ion + Pyruvaldehyde + NADH > D-Lactaldehyde + NAD Pyruvaldehyde + NAD + Water <> Pyruvic acid + NADH + Hydrogen ion D-Lactaldehyde + NAD <> Pyruvaldehyde + NADH + Hydrogen ion Aminoacetone + Water + Oxygen <> Pyruvaldehyde + Ammonia + Hydrogen peroxide S-Lactoylglutathione <> Glutathione + Pyruvaldehyde Aminoacetone + Water + Oxygen > Hydrogen ion + Pyruvaldehyde + Ammonia + Hydrogen peroxide S-Lactoylglutathione < Pyruvaldehyde + Glutathione D-Lactic acid + Hydrogen ion < Pyruvaldehyde + Water Dihydroxyacetone phosphate > Pyruvaldehyde + Phosphate Lactaldehyde + NADP < Pyruvaldehyde + NADPH + Hydrogen ion Hydrogen ion + Pyruvaldehyde + NADH acetol + NAD D-Lactic acid > Pyruvaldehyde + Water S-Lactoylglutathione > Glutathione + Pyruvaldehyde Dihydroxyacetone phosphate > Pyruvaldehyde + Inorganic phosphate D-Lactic acid <> Pyruvaldehyde + Water Pyruvaldehyde + NADPH + Hydrogen ion <> Hydroxyacetone + NADP Pyruvaldehyde + Water > D-Lactic acid + Hydrogen ion Pyruvaldehyde + NADPH + Hydrogen ion > Lactaldehyde + NADP Aminoacetone + Oxygen + Water > Hydrogen peroxide + Ammonium + Pyruvaldehyde Pyruvaldehyde + Glutathione > S-Lactoylglutathione D-Lactic acid <> Pyruvaldehyde + Water Glutathione + Pyruvaldehyde <> S-Lactoylglutathione | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Zhang, Jing-An; Chen, Yu-Ping. Synthesis of pyruvaldehyde. Jingxi Huagong (2000), 17(9), 507-510. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in methylglyoxal synthase activity
- Specific function:
- Glycerone phosphate = methylglyoxal + phosphate
- Gene Name:
- mgsA
- Uniprot ID:
- P0A731
- Molecular weight:
- 16918
Reactions
Glycerone phosphate = methylglyoxal + phosphate. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the NAD-dependent oxidation of glycerol to dihydroxyacetone (glycerone). Allows microorganisms to utilize glycerol as a source of carbon under anaerobic conditions. In E.coli, an important role of gldA is also likely to regulate the intracellular level of dihydroxyacetone by catalyzing the reverse reaction, i.e. the conversion of dihydroxyacetone into glycerol. Possesses a broad substrate specificity, since it is also able to oxidize 1,2-propanediol and to reduce glycolaldehyde, methylglyoxal and hydroxyacetone into ethylene glycol, lactaldehyde and 1,2-propanediol, respectively
- Gene Name:
- gldA
- Uniprot ID:
- P0A9S5
- Molecular weight:
- 38712
Reactions
Glycerol + NAD(+) = glycerone + NADH. |
- General function:
- Involved in lactoylglutathione lyase activity
- Specific function:
- Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione
- Gene Name:
- gloA
- Uniprot ID:
- P0AC81
- Molecular weight:
- 14920
Reactions
(R)-S-lactoylglutathione = glutathione + methylglyoxal. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Acts on lactaldehyde as well as other aldehydes
- Gene Name:
- aldA
- Uniprot ID:
- P25553
- Molecular weight:
- 52272
Reactions
(S)-lactaldehyde + NAD(+) + H(2)O = (S)-lactate + NADH. |
Glycolaldehyde + NAD(+) + H(2)O = glycolate + NADH. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG)
- Gene Name:
- dkgB
- Uniprot ID:
- P30863
- Molecular weight:
- 29437
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH. |
- General function:
- Involved in copper ion binding
- Specific function:
- The enzyme prefers aromatic over aliphatic amines
- Gene Name:
- tynA
- Uniprot ID:
- P46883
- Molecular weight:
- 84378
Reactions
RCH(2)NH(2) + H(2)O + O(2) = RCHO + NH(3) + H(2)O(2). |
2-phenylethylamine + H(2)O + O(2) = phenylacetaldehyde + NH(3) + H(2)O(2). |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
- Gene Name:
- ghrA
- Uniprot ID:
- P75913
- Molecular weight:
- 35343
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH. |
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG). It is also capable of stereoselective -keto ester reductions on ethyl acetoacetate and other 2-substituted derivatives
- Gene Name:
- dkgA
- Uniprot ID:
- Q46857
- Molecular weight:
- 31109
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH. |
- General function:
- Energy production and conversion
- Specific function:
- Specific function unknown
- Gene Name:
- yghZ
- Uniprot ID:
- Q46851
- Molecular weight:
- 38832
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Specific function unknown
- Gene Name:
- yeaE
- Uniprot ID:
- P76234
- Molecular weight:
- 30986
- General function:
- Not Available
- Specific function:
- Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus. Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus.
- Gene Name:
- hchA
- Uniprot ID:
- P31658
- Molecular weight:
- Not Available
Reactions
(R)-lactate = methylglyoxal + H(2)O. |
(R)-lactate = methylglyoxal + H(2)O. |