Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:55:58 -0600 |
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Update Date | 2015-06-03 15:54:15 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | (S)-b-aminoisobutyric acid |
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Description | Beta-Aminoisobutyric acid is a non-protein amino acid originating from the catabolism of thymine and valine. Beta-Aminoisobutyric acid occurs in two isomeric forms. The S-enantiomer of beta-Aminoisobutyric acid is predominantly derived from the catabolism of valine. It has been suggested that an altered homoeostasis of b-alanine underlies some of the abnormalities with a dihydropyrimidine dehydrogenase (DPD). DPD constitutes the first step of the pyrimidine degradation pathway, in which the pyrimidine bases uracil and thymine are catabolized to b-alanine and the R-enantiomer of beta-Aminoisobutyric acid respectively. In normal situation with an intact pyrimidine degradation pathway, R-methylmalonic acid semialdehyde can be synthesized directly from the catabolism of thymine. Hence, there might be less cross-over between the valine and thymine pathway, allowing the conversion of S-methylmalonic acid semialdehyde into S-beta-Aminoisobutyric acid and the subsequent accumulation of S-beta-Aminoisobutyric acid. (PMID: 14705962, 14292857, 14453202) |
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Structure | |
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Synonyms: | - (+)-a-Methyl-b-alanine
- (+)-alpha-Methyl-beta-alanine
- (+)-b-Aminoisobutyrate
- (+)-b-Aminoisobutyric acid
- (+)-beta-Aminoisobutyrate
- (+)-beta-Aminoisobutyric acid
- (+)-α-Methyl-β-alanine
- (+)-β-Aminoisobutyrate
- (+)-β-Aminoisobutyric acid
- (S)-3-amino-2-methyl-Propanoate
- (S)-3-amino-2-methyl-Propanoic acid
- (S)-3-Amino-2-methylpropanoate
- (S)-3-Amino-2-methylpropanoic acid
- (S)-3-Amino-isobutanoate
- (S)-3-Amino-isobutanoic acid
- (S)-3-Amino-isobutyrate
- (S)-3-Amino-isobutyric acid
- (S)-b-Aminoisobutyrate
- (S)-b-Aminoisobutyric acid
- (S)-beta-Aminoisobutyrate
- (S)-beta-Aminoisobutyric acid
- (S)-β-Aminoisobutyrate
- (S)-β-Aminoisobutyric acid
- L-2-Methyl-b-Alanine
- L-2-Methyl-beta-Alanine
- L-2-Methyl-β-alanine
- L-3-Amino-2-methylpropanoate
- L-3-Amino-2-methylpropanoic acid
- L-3-Amino-2-methylpropionate
- L-3-Amino-2-methylpropionic acid
- L-3-Amino-isobutanoate
- L-3-Amino-isobutanoic acid
- L-3-Amino-isobutyrate
- L-3-Amino-isobutyric acid
- L-b-Aminoisobutyrate
- L-b-Aminoisobutyric acid
- L-beta-Aminoisobutyrate
- L-beta-Aminoisobutyric acid
- L-β-Aminoisobutyrate
- L-β-Aminoisobutyric acid
- S-b-Aminoisobutyrate
- S-b-Aminoisobutyric acid
- S-beta-Aminoisobutyrate
- S-beta-Aminoisobutyric acid
- S-β-Aminoisobutyrate
- S-β-Aminoisobutyric acid
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Chemical Formula: | C4H9NO2 |
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Weight: | Average: 103.1198 Monoisotopic: 103.063328537 |
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InChI Key: | QCHPKSFMDHPSNR-VKHMYHEASA-N |
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InChI: | InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1 |
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CAS number: | 4249-19-8 |
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IUPAC Name: | (2S)-3-amino-2-methylpropanoic acid |
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Traditional IUPAC Name: | L-β-aminoisobutyric acid |
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SMILES: | C[C@@H](CN)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Beta amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Beta amino acid or derivatives
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Amine
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen 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: | 0 |
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Melting point: | 175-177 °C |
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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: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - Valine, leucine and isoleucine degradation ec00280
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EcoCyc Pathways: | Not Available |
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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 | splash10-001i-9000000000-59e52601f90d8e636d61 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00ar-9200000000-0eb92539979a9fa36dbd | 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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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-0udi-1900000000-aaccebe5d4a868bc32bf | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-0udi-2900000000-4f4e49fe169d5c21efc1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-0udi-4900000000-f32e82420f5efb60456e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0uk9-6900000000-cb0ef82b397e24372142 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0uk9-8900000000-31fc31847c8771693d15 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0fk9-9600000000-6379643466e30660a05b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, negative | splash10-00di-9300000000-97e8a7125780e41fceaf | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-05fr-9200000000-8f0488fe62603d121536 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-0ab9-9100000000-84e07fbee3e332502265 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, negative | splash10-0a4i-9000000000-3634b730902e2e080b56 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 7V, negative | splash10-00di-9000000000-1b9078e3902a11473fa0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-0udi-1900000000-76d19f44560e6b1b6f80 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-0udi-1900000000-bd4e85f35b448a2b7540 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-0udi-2900000000-b1371ec53be10ec9c411 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udi-3900000000-d16b3475fcdfed5038d5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udi-4900000000-cd34930bbcb805c7525f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udr-5900000000-4b73ac1046680185a981 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udr-6900000000-a911da27982a560a6cf1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udr-8900000000-91a255aae27e4e4aabb8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f79-9300000000-30669ed04aadf3d3f040 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000l-9000000000-ca65637476e64152c44e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-04d1648391d3f90db226 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-3900000000-ec54fcce079024a62344 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zfr-9500000000-0394f399cdf5df93c5df | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-d0c495c908ed905558a2 | 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: | - KAKIMOTO Y, ARMSTRONG MD: The preparation and isolation of D-(-)-beta-aminoisobutyric acid. J Biol Chem. 1961 Dec;236:3283-6. Pubmed: 14453202
- KAKIMOTO Y, KANAZAWA A, SANO I: IDENTIFICATION OF D(-)-BETA-AMINOISOBUTYRIC ACID IN HUMAN LIVER. Biochim Biophys Acta. 1965 Feb 15;97:376-7. Pubmed: 14292857
- 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
- Roe CR, Struys E, Kok RM, Roe DS, Harris RA, Jakobs C: Methylmalonic semialdehyde dehydrogenase deficiency: psychomotor delay and methylmalonic aciduria without metabolic decompensation. Mol Genet Metab. 1998 Sep;65(1):35-43. Pubmed: 9787093
- Van Kuilenburg, A. B., Stroomer, A. E., Van Lenthe, H., Abeling, N. G., Van Gennip, A. H. (2004). "New insights in dihydropyrimidine dehydrogenase deficiency: a pivotal role for beta-aminoisobutyric acid?" Biochem J 379:119-124. Pubmed: 14705962
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Synthesis Reference: | Alauddin, Mian M.; Fissekis, John D.; Conti, Peter S. a-Alkylation of amino acid derivatives: synthesis and chiral resolution of [11C]b-aminoisobutyric acid. Nuclear Medicine and Biology (1997), 24(8), 771-775. |
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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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