Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:20:42 -0600 |
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Update Date | 2015-06-03 17:19:02 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | (R) 2,3-Dihydroxy-3-methylvalerate |
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Description | (R) 2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-methylvalerate is generated from 3-Hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC:4.2.1.9). |
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Structure | |
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Synonyms: | - (2R,3R)-2,3-dihydroxy-3-methylpentanoate
- (2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
- (R) 2,3-Dihydroxy-3-methylvaleric acid
- (R)-2,3-Dihydroxy-3-methylpentanoate
- (R)-2,3-Dihydroxy-3-methylpentanoic acid
- (R)-2,3-Dihydroxy-3-methylvalerate
- (R)-2,3-Dihydroxy-3-methylvaleric acid
- 1-Keto-2-methylvalerate
- 1-Keto-2-methylvaleric acid
- 2,3-Dihydroxy-3-Methyl-Valerate
- 2,3-Dihydroxy-3-Methyl-Valeric acid
- 2,3-Dihydroxy-3-methylpentanoate
- 2,3-Dihydroxy-3-methylpentanoic acid
- 2,3-Dihydroxy-Valerianate
- 2,3-Dihydroxy-Valerianic Acid
- 4,5-Dideoxy-3-C-methyl-pentonate
- 4,5-Dideoxy-3-C-methyl-pentonic acid
- a,b-Dihydroxy-b-methylvalerate
- a,b-Dihydroxy-b-methylvaleric acid
- Alpha,beta-Dihydroxy-beta-methylvalerate
- Alpha,beta-Dihydroxy-beta-methylvaleric acid
- CID8
- DMV
- α,β-Dihydroxy-β-methylvalerate
- α,β-Dihydroxy-β-methylvaleric acid
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Chemical Formula: | C6H12O4 |
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Weight: | Average: 148.1571 Monoisotopic: 148.073558872 |
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InChI Key: | PDGXJDXVGMHUIR-UJURSFKZSA-N |
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InChI: | InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1 |
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CAS number: | 562-43-6 |
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IUPAC Name: | (2R,3R)-2,3-dihydroxy-3-methylpentanoic acid |
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Traditional IUPAC Name: | (2R,3R)-2,3-dihydroxy-3-methylpentanoic acid |
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SMILES: | CC[C@@](C)(O)[C@@H](O)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Hydroxy fatty acids |
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Alternative Parents | |
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Substituents | - Branched fatty acid
- Methyl-branched fatty acid
- Short-chain hydroxy acid
- Hydroxy fatty acid
- Alpha-hydroxy acid
- Hydroxy acid
- Monosaccharide
- Tertiary alcohol
- 1,2-diol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organooxygen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | (R) 2,3-Dihydroxy-3-methylvalerate > 3-Methyl-2-oxovaleric acid + Water2-Aceto-2-hydroxy-butyrate + Hydrogen ion + NADPH <> (R) 2,3-Dihydroxy-3-methylvalerate + NADP(R) 2,3-Dihydroxy-3-methylvalerate + NADP <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate + NADPH + Hydrogen ion(R) 2,3-Dihydroxy-3-methylvalerate <> 3-Methyl-2-oxovaleric acid + Water(R) 2,3-Dihydroxy-3-methylvalerate + NADP <> Hydrogen ion + 2-Aceto-2-hydroxy-butyrate + NADPH(R) 2,3-Dihydroxy-3-methylvalerate + NADP > 2-Aceto-2-hydroxy-butyrate + NADPH(R)-2,3-Dihydroxy-isovalerate + Hydrogen ion + NADPH + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate2-Aceto-2-hydroxy-butyrate + NADPH + Hydrogen ion + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate(R) 2,3-Dihydroxy-3-methylvalerate > Water + 3-Methyl-2-oxovaleric acid + 3-Methyl-2-oxovaleric acid |
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SMPDB Pathways: | Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvate | PW000978 | | Valine Biosynthesis | PW000812 | | isoleucine biosynthesis | PW000818 | |
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KEGG Pathways: | - Valine, leucine and isoleucine biosynthesis ec00290
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9000000000-d382043e81321879e92e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-00tb-9464000000-0280de9eaa4c12333997 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05aj-7900000000-ed4255c918254a1dc462 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0kar-9600000000-420faa83ea76001db2e9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-9000000000-393b15b5811231e32693 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udj-2900000000-d582074beb8b89338fa5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9400000000-5ee3e425ebda8358d337 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05g0-9000000000-db72ead6bd87a129b325 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0h32-2900000000-0dc4c2a3c02313bed77c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-431db2e8dea59bdd5c38 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-349f8877717c1418480e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-81689c0553421abfcd88 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9100000000-d9815468ea9acf930e9e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9100000000-f894bf4ab44aaac79501 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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