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Identification |
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YMDB ID | YMDB00086 |
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Name | Citric acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Citric acid, also known as anhydrous citrate or citronensaeure, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Citric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Citric acid exists in all living species, ranging from bacteria to humans. Citric acid is a potentially toxic compound. |
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Structure | |
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Synonyms | - 2-Hydroxy-1,2,3-propanetricarboxylate
- 2-hydroxy-1,2,3-propanetricarboxylate(3-)
- 2-Hydroxy-1,2,3-propanetricarboxylic acid
- 2-hydroxy-1,2,3-propanetricarboxylic acid, ion(3-)
- 2-hydroxytricarballylate
- 3-Carboxy-3-hydroxypentane-1,5-dioate
- 3-Carboxy-3-hydroxypentane-1,5-dioic acid
- Aciletten
- Anhydrous citrate
- Anhydrous citric acid
- beta-Hydroxytricarballylate
- beta-Hydroxytricarballylic acid
- cit
- cit(3-)
- Citraclean
- Citrate
- CITRATE ANION
- Citretten
- Citric acid
- Citro
- Hydrocerol A
- Kyselina citronova
- Suby G
- Uro-trainer
- 2-Hydroxytricarballylic acid
- Citronensaeure
- e330
- H3Cit
- Citric acid anhydrous
- Citrate anhydrous
- Chemfill
- e 330
- Acid monohydrate, citric
- Monohydrate, citric acid
- Citric acid, anhydrous
- Citric acid monohydrate
- Uralyt u
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CAS number | 77-92-9 |
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Weight | Average: 192.1235 Monoisotopic: 192.02700261 |
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InChI Key | KRKNYBCHXYNGOX-UHFFFAOYSA-N |
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InChI | InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12) |
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IUPAC Name | 2-hydroxypropane-1,2,3-tricarboxylic acid |
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Traditional IUPAC Name | citric acid |
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Chemical Formula | C6H8O7 |
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SMILES | [H]OC(=O)C([H])([H])C(O[H])(C(=O)O[H])C([H])([H])C(=O)O[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. |
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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 | Tricarboxylic acids and derivatives |
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Direct Parent | Tricarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Tricarboxylic acid or derivatives
- Hydroxy acid
- Alpha-hydroxy acid
- Tertiary alcohol
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | 153 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 592 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)] | PhysProp | LogP | -1.64 [AVDEEF,A (1997)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Mitochondrion
- Peroxisome
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Organoleptic Properties | |
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SMPDB Pathways | |
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KEGG Pathways | Citrate cycle (TCA cycle) | ec00020 | | Glyoxylate and dicarboxylate metabolism | ec00630 | |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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2400 ± 100 µM | Minimal medium supplemented with ammonia salts | aerobic;resting cells | Baker's yeast | PMID: 4578278 | 13500 ± 9500 µM | Minimal medium supplemented with ammonia salts and glucose | aerobic and anaerobic;resting cells | Baker's yeast | PMID: 4578278 | 700 ± 0 µM | Minimal medium supplemented with ammonia salts and (glucose or galactose) | aerobic;growing cells | Baker's yeast | PMID: 4578278 | 5200 ± 500 µM | Synthetic medium with 2% glucose | aerobic;growing cells | Baker's yeast | PMID: 6229402 | 210 ± 10 µM | Synthetic medium with 2% glucose | aerobic;resting cells | Baker's yeast | PMID: 6229402 | 1500 ± 400 µM | Synthetic medium with 2% glucose | anaerobic;resting cells | Baker's yeast | PMID: 6229402 | 3700 ± 700 µM | Synthetic medium with 2% galactose | aerobic;resting cells | Baker's yeast | PMID: 6229402 | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0002-0941000000-c310fda0e6a19bf6ae40 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0002-0941000000-f1dfda3e9abc7cfb6b2a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-006t-0952000000-ba3a1a80815f65afd05c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0951000000-48857e9baebe16d9fc8d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-00di-9531000000-b6fd7d038634694f0873 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-00di-0593000000-b193bbba8c0cefdfe42a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0941000000-c310fda0e6a19bf6ae40 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0941000000-f1dfda3e9abc7cfb6b2a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-006t-0952000000-ba3a1a80815f65afd05c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0951000000-48857e9baebe16d9fc8d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9531000000-b6fd7d038634694f0873 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00di-0593000000-b193bbba8c0cefdfe42a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0941000000-573230e47a4efb1e36a5 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002k-6900000000-d1a61a52f6efdec3101a | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-02ib-6019300000-6d5ebea10441c6d4149a | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-03di-2900000000-956001b034bbc0b7da96 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-000l-9100000000-55e34e2c1616942fd4f2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-000f-9000000000-7b8be3e90a4daf85f04a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-0911200000-af80d22f720facc4813a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-014i-9000000000-6f4fedbb19821898fb22 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-8eff68ab89f7ce2262be | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0fsi-0019300000-b370c4c3dd656c8eb729 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-0912100000-05e8ceb6dd97f7b9af98 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-014i-9000000000-e4b67745443c48a63bd6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-92536abec982e0a653a0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0190000000-35772df08490f451d828 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0006-0900000000-35856cc258368d13e1ff | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03di-3900000000-7170fdcb9749e6d6c2fb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-01p9-9500000000-9a502981b0a9e1ea35ad | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-000i-9100000000-ed0c86b90e1f4966d025 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4r-9000000000-b8a975c2d639d8c91afb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03di-2900000000-30970a4250098e148658 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0900000000-a587dddf188152c5d7b0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-3900000000-7170fdcb9749e6d6c2fb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-01p9-9500000000-9a502981b0a9e1ea35ad | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9100000000-42a125e9128ce21bd785 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4r-9000000000-b8a975c2d639d8c91afb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-03di-0900000000-32af4c1bf55ea1563e53 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-014i-9000000000-6f4fedbb19821898fb22 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-03di-0900000000-8eff68ab89f7ce2262be | JSpectraViewer | MoNA | MS | Mass Spectrum (Electron Ionization) | splash10-002f-9400000000-fb757b614278bb898b54 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Lawrence, C. L., Botting, C. H., Antrobus, R., Coote, P. J. (2004). "Evidence of a new role for the high-osmolarity glycerol mitogen-activated protein kinase pathway in yeast: regulating adaptation to citric acid stress." Mol Cell Biol 24:3307-3323.15060153
- Sandor, A., Johnson, J. H., Srere, P. A. (1994). "Cooperation between enzyme and transporter in the inner mitochondrial membrane of yeast. Requirement for mitochondrial citrate synthase for citrate and malate transport in Saccharomyces cerevisiae." J Biol Chem 269:29609-29612.7961948
- Kispal, G., Srere, P. A. (1991). "Studies on yeast peroxisomal citrate synthase." Arch Biochem Biophys 286:132-137.1897942
- Velot, C., Lebreton, S., Morgunov, I., Usher, K. C., Srere, P. A. (1999). "Metabolic effects of mislocalized mitochondrial and peroxisomal citrate synthases in yeast Saccharomyces cerevisiae." Biochemistry 38:16195-16204.10587442
- Jia, Y. K., Becam, A. M., Herbert, C. J. (1997). "The CIT3 gene of Saccharomyces cerevisiae encodes a second mitochondrial isoform of citrate synthase." Mol Microbiol 24:53-59.9140965
- Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
- Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
- Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
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Synthesis Reference: | Evans, D. W. S. Hydrolysis of ethyl methylenecitrate [5,5-bis(ethoxycarbonylmethyl)-1,3-dioxolan-4-one] and an attempted synthesis of agaric acid. Journal of the Chemical Society (1959), 1313-14. |
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