Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:49 UTC |
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HMDB ID | HMDB0000426 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Citramalic acid |
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Description | Citramalic acid, also known as 2-Methylmalic acid, is an analog of malic acid. The structure of citramalic acid is similar to the structure of malic acid except it has an extra CH3 group on position 2. It is also classified as a 2-hydroxydicarboxylic acid. Citramalic acid exists in two isomers, L-citramalic acid and D-citramalic acid. The L-isomer is more biologically relevant isomer. Citramalic acid is found in almost all living organisms from microbes to plants to humans although citramalate is primarily produced from bacteria. L-citramalic acid was first isolated from the peel of apples in 1954 (PMID: 13160011 ). It has also been isolated in wine and other ripening fruit (PMID: 13807713 ). Citramalic acid can inhibit the production of malic acid. Citramalic acid is also an important microbial metabolite and has been found to be a byproduct of Saccharomyces yeast species, as well as Propionibacterium acnes and Aspergillus niger (PMID: 31827810 ) (http://drweyrich.weyrich.com/labs/oat.html) (PMID: 7628083 ). Citramalic acid is a component of the C5-branched dibasic acid metabolism pathway. It can be broken down by the enzyme citramalate lyase, which converts citramalate to acetate and pyruvate. Citramalate synthase is an enzyme found in bacteria that synthesizes citramalic acid from acetyl-CoA, pyruvate and water. Citramalic acid may have a useful role in medical diagnoses. It has been found in the urine of two brothers with autistic features (PMID: 7628083 ). Citramalic acid can also be used as a urinary marker for gut dysbiosis (PMID: 31669633 ). Dysbiosis is a disorder of the bacterial flora of the human digestive tract. It is usually diagnosed clinically by direct detection of an abnormal pattern of the intestinal microbiota. |
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Structure | InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9) |
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Synonyms | Value | Source |
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(+-)-2-Hydroxy-2-methylsuccinic acid | ChEBI | 2-Hydroxy-2-methylbutanedioic acid | ChEBI | 2-Hydroxy-2-methylsuccinic acid | ChEBI | 2-Methylmalic acid | ChEBI | alpha-Hydroxypyrotartaric acid | ChEBI | Citramalic acids | ChEBI | (+-)-2-Hydroxy-2-methylsuccinate | Generator | 2-Hydroxy-2-methylbutanedioate | Generator | 2-Hydroxy-2-methylsuccinate | Generator | 2-Methylmalate | Generator | a-Hydroxypyrotartarate | Generator | a-Hydroxypyrotartaric acid | Generator | alpha-Hydroxypyrotartarate | Generator | Α-hydroxypyrotartarate | Generator | Α-hydroxypyrotartaric acid | Generator | Citramalate | Generator | (b)-2-Methylmalate | HMDB | (b)-2-Methylmalic acid | HMDB | (b)-Citramalate | HMDB | (b)-Citramalic acid | HMDB | (R,S)-(b)-Citramalate | HMDB | (R,S)-(b)-Citramalic acid | HMDB | (R,S)-b-Methylmalate | HMDB | (R,S)-b-Methylmalic acid | HMDB | (R,S)-beta-Methylmalate | HMDB | (R,S)-beta-Methylmalic acid | HMDB | 2-Deoxy-3-C-methyltetrarate | HMDB | 2-Deoxy-3-C-methyltetraric acid | HMDB | 2-Hydroxy-2-methyl-(b)-butanedioate | HMDB | 2-Hydroxy-2-methyl-(b)-butanedioic acid | HMDB | 2-Hydroxy-2-methyl-butanedioate | HMDB | 2-Hydroxy-2-methyl-butanedioic acid | HMDB | 2-Methyl-(b)-malate | HMDB | 2-Methyl-(b)-malic acid | HMDB | DL-Citramalate | HMDB | DL-Citramalic acid | HMDB | Citramalate, (+-)-isomer | HMDB | Citramalate, (R)-isomer | HMDB | Citramalate, (S)-isomer | HMDB | alpha-Methylmalate | HMDB | (R)-2-Hydroxy-2-methylbutanedioate | HMDB | Citramalic acid | KEGG |
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Chemical Formula | C5H8O5 |
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Average Molecular Weight | 148.114 |
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Monoisotopic Molecular Weight | 148.037173366 |
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IUPAC Name | 2-hydroxy-2-methylbutanedioic acid |
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Traditional Name | citramalate, (+-)- |
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CAS Registry Number | 597-44-4 |
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SMILES | CC(O)(CC(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9) |
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InChI Key | XFTRTWQBIOMVPK-UHFFFAOYSA-N |
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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
- Dicarboxylic acid or derivatives
- Hydroxy acid
- Tertiary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 107 - 111 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000000 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Citramalic acid,1TMS,isomer #1 | CC(CC(=O)O)(O[Si](C)(C)C)C(=O)O | 1382.7 | Semi standard non polar | 33892256 | Citramalic acid,1TMS,isomer #2 | CC(O)(CC(=O)O[Si](C)(C)C)C(=O)O | 1322.7 | Semi standard non polar | 33892256 | Citramalic acid,1TMS,isomer #3 | CC(O)(CC(=O)O)C(=O)O[Si](C)(C)C | 1302.0 | Semi standard non polar | 33892256 | Citramalic acid,2TMS,isomer #1 | CC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O | 1444.5 | Semi standard non polar | 33892256 | Citramalic acid,2TMS,isomer #2 | CC(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1416.5 | Semi standard non polar | 33892256 | Citramalic acid,2TMS,isomer #3 | CC(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1368.5 | Semi standard non polar | 33892256 | Citramalic acid,3TMS,isomer #1 | CC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1482.9 | Semi standard non polar | 33892256 | Citramalic acid,1TBDMS,isomer #1 | CC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O | 1613.5 | Semi standard non polar | 33892256 | Citramalic acid,1TBDMS,isomer #2 | CC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O | 1587.4 | Semi standard non polar | 33892256 | Citramalic acid,1TBDMS,isomer #3 | CC(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C | 1594.5 | Semi standard non polar | 33892256 | Citramalic acid,2TBDMS,isomer #1 | CC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O | 1881.4 | Semi standard non polar | 33892256 | Citramalic acid,2TBDMS,isomer #2 | CC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1867.0 | Semi standard non polar | 33892256 | Citramalic acid,2TBDMS,isomer #3 | CC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1833.5 | Semi standard non polar | 33892256 | Citramalic acid,3TBDMS,isomer #1 | CC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2137.2 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-000l-9200000000-d88cf81bb63b8badd74d | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (3 TMS) - 70eV, Positive | splash10-00gs-8492000000-d1c8fb9235f1de536d15 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citramalic acid GC-MS (TBDMS_3_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid Quattro_QQQ 10V, Negative-QTOF (Annotated) | splash10-000j-7900000000-efbe2adf2c82decc64a6 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid Quattro_QQQ 25V, Negative-QTOF (Annotated) | splash10-052u-9000000000-3754186783f820cbff7c | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid Quattro_QQQ 40V, Negative-QTOF (Annotated) | splash10-052o-9000000000-0656e8e194378442727f | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid LC-ESI-ITFT , negative-QTOF | splash10-0002-2900000000-be1cc6b0ea685f5d7ac2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid LC-ESI-IT , negative-QTOF | splash10-002r-8900000000-7dd192ed79cd2d306ea5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid , negative-QTOF | splash10-000i-9500000000-c96a62314140c10f1245 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 50V, Negative-QTOF | splash10-0002-2900000000-716fb416386753113137 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 40V, Negative-QTOF | splash10-0a4l-9000000000-20ae5f1dfa6847e56e0d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 20V, Negative-QTOF | splash10-000i-9000000000-4bc688d98054e464cf07 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 30V, Negative-QTOF | splash10-0a4r-9000000000-61294657ce4e2d5d6d05 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 10V, Negative-QTOF | splash10-000i-9400000000-d027e4da9369388ea3c2 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 40V, Negative-QTOF | splash10-0a4l-9000000000-e7930822f64c0c43d7c0 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 35V, Negative-QTOF | splash10-000i-9500000000-2e922f07663d3c399240 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 10V, Negative-QTOF | splash10-000i-9400000000-b372db83cd99e22fb0ac | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citramalic acid 20V, Negative-QTOF | splash10-000i-9000000000-093483f4bf2d387fa405 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 10V, Positive-QTOF | splash10-001a-5900000000-437d36fe16a8d6f79c68 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 20V, Positive-QTOF | splash10-000i-9200000000-6aed3a8e654948bbd5e8 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 40V, Positive-QTOF | splash10-000i-9000000000-31c6a41b79f5b68fa431 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 10V, Negative-QTOF | splash10-0uds-4900000000-0d782e5134753ac75aeb | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 20V, Negative-QTOF | splash10-0zg0-9800000000-79154974b5c30f915ea5 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 40V, Negative-QTOF | splash10-0a4i-9100000000-16648250719da0016f96 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 10V, Negative-QTOF | splash10-0f79-7900000000-7ad97a16a3c93f065dc0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 20V, Negative-QTOF | splash10-0pbi-9200000000-5a2fa29950e165d19eee | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 40V, Negative-QTOF | splash10-0006-9000000000-6e51c64fc7bc0e025373 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Citramalic acid 10V, Positive-QTOF | splash10-0019-7900000000-8d007c21807d42c8e41b | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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General References | - Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. [PubMed:7628083 ]
- HULME AC: The oxidation of citramalic acid and beta-hydroxyglutaric acid to acetoacetic acid and the possible significance of citramalic acid in plant metabolism. Biochim Biophys Acta. 1954 May;14(1):44-51. [PubMed:13160012 ]
- Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]
- Perlman S, Carr SA: Citramalic acid in cerebrospinal fluid of patients with bacterial meningitis. Clin Chem. 1984 Jul;30(7):1209-12. [PubMed:6145530 ]
- Greter J, Lindstedt S, Seeman H, Steen G: 2-hydroxy-2-methylsuccinic acid--a urinary metabolite in propionyl-CoA carboxylase deficiency. Clin Chim Acta. 1980 Sep 8;106(1):103-6. [PubMed:7408203 ]
- HULME AC: The isolation of l-citramalic acid from the peel of the apple fruit. Biochim Biophys Acta. 1954 May;14(1):36-43. doi: 10.1016/0006-3002(54)90127-4. [PubMed:13160011 ]
- CARLES J: [On the decarboxylations in wine and the appearance of citramalic acid]. Rev Esp Fisiol. 1959 Sep;15:193-9. [PubMed:13807713 ]
- Hossain AH, Hendrikx A, Punt PJ: Identification of novel citramalate biosynthesis pathways in Aspergillus niger. Fungal Biol Biotechnol. 2019 Nov 19;6:19. doi: 10.1186/s40694-019-0084-7. eCollection 2019. [PubMed:31827810 ]
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