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Identification |
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YMDB ID | YMDB00152 |
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Name | L-Valine |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Valine (abbreviated as Val or V) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a nonpolar branched chain amino acid, because of the hydrophobic nature of its branched alkyl side chain. S. cerevisiae degrade the branched-chain amino acids (valine, leucine, and iso-leucine) via the Ehrlich pathway. This pathway consists of 3 steps: 1) deamination of the amino acid to the corresponding alpha-keto acid; 2) decarboxylation of the resulting alpha-keto acid to the respective aldehyde; and, 3) reduction of the aldehyde to form the corresponding long chain or complex alcohol, known as a fusel alcohol or fusel oil. Fusel alcohols are important flavor and aroma compounds in yeast-fermented food products and beverages. Each of the three steps in branched-chain amino acid degradation can be catalyzed by more than one isozyme; which enzyme is used appears to depend on the amino acid, the carbon source and the stage of growth of the culture. |
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Structure | |
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Synonyms | - (2S)-2-Amino-3-methylbutanoate
- (2S)-2-Amino-3-methylbutanoic acid
- (S)-2-amino-3-methyl-Butanoate
- (S)-2-amino-3-methyl-Butanoic acid
- (S)-2-Amino-3-methylbutanoate
- (S)-2-Amino-3-methylbutanoic acid
- (S)-2-Amino-3-methylbutyrate
- (S)-2-Amino-3-methylbutyric acid
- (S)-a-Amino-b-methylbutyrate
- (S)-a-Amino-b-methylbutyric acid
- (S)-alpha-Amino-beta-methylbutyrate
- (S)-alpha-Amino-beta-methylbutyric acid
- (S)-Valine
- 2-Amino-3-methylbutanoate
- 2-Amino-3-methylbutanoic acid
- 2-Amino-3-methylbutyrate
- 2-Amino-3-methylbutyric acid
- L-(+)-a-Aminoisovalerate
- L-(+)-a-Aminoisovaleric acid
- L-(+)-alpha-Aminoisovalerate
- L-(+)-alpha-Aminoisovaleric acid
- L-a-Amino-b-methylbutyrate
- L-a-Amino-b-methylbutyric acid
- L-alpha-Amino-beta-methylbutyrate
- L-alpha-Amino-beta-methylbutyric acid
- L-valine
- valine
- L-Valin
- V
- Val
- L-(+)-Α-aminoisovalerate
- L-(+)-Α-aminoisovaleric acid
- L-Α-amino-β-methylbutyrate
- L-Α-amino-β-methylbutyric acid
- L Valine
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CAS number | 72-18-4 |
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Weight | Average: 117.1463 Monoisotopic: 117.078978601 |
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InChI Key | KZSNJWFQEVHDMF-BYPYZUCNSA-N |
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InChI | InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1 |
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IUPAC Name | (2S)-2-amino-3-methylbutanoic acid |
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Traditional IUPAC Name | L-valine |
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Chemical Formula | C5H11NO2 |
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SMILES | [H]OC(=O)[C@@]([H])(N([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Valine and derivatives |
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Alternative Parents | |
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Substituents | - Valine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Branched fatty acid
- Methyl-branched fatty acid
- Fatty acid
- Fatty acyl
- Amino acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- 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 | 295-300 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 58.5 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP | -2.26 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - extracellular
- mitochondrion
- cytoplasm
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Organoleptic Properties | |
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SMPDB Pathways | |
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KEGG Pathways | Pantothenate and CoA biosynthesis | ec00770 |  | Propanoate metabolism | ec00640 |  | Valine, leucine and isoleucine biosynthesis | ec00290 |  | Valine, leucine and isoleucine degradation | ec00280 |  |
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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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2276 ± 46 µM | YPD media | aerobic | Baker's yeast | PMID: 7654310 | 1839 ± 37 µM | YPG media | aerobic | Baker's yeast | PMID: 7654310 | 788 ± 16 µM | SD media | aerobic | Baker's yeast | PMID: 7654310 | 876 ± 18 µM | SG media | aerobic | Baker's yeast | PMID: 7654310 | 525 ± 10 µM | M (molasses) | aerobic | Baker's yeast | PMID: 7654310 | 2802 ± 56 µM | MA (molasses) | aerobic | Baker's yeast | PMID: 7654310 | 1226 ± 24 µM | MB (molasses) | aerobic | Baker's yeast | PMID: 7654310 | 2014 ± 40 µM | MAB (molasses) | aerobic | Baker's yeast | PMID: 7654310 | 2770 ± 139 µM | YEB media with 0.5 mM glucose | aerobic | Baker's yeast | Experimentally Determined Not Available | 3610 ± 664 µM | Synthetic medium with 20 g/L glucose | aerobic | Baker's yeast | PMID: 12584756 | 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) (2 TMS) | splash10-0006-0910000000-23bfcf2795f71f458bda | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0006-0920000000-7892bb9d4d9afcc23410 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0006-0910000000-f2491152816b9c5dc7ed | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-0znj-1900000000-7c976d7c11a402db399f | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00dl-8910000000-78e8ee971ad7298c23cd | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-00di-9200000000-805e6724e5181af78c81 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0006-0910000000-a212771a5ea868139d5a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-059t-0900000000-7b8e4e98ac9158bf26d9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-0910000000-9079324093be9a14d47a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0006-0910000000-23bfcf2795f71f458bda | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0006-0920000000-7892bb9d4d9afcc23410 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0006-0910000000-f2491152816b9c5dc7ed | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0znj-1900000000-7c976d7c11a402db399f | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-QQ (Non-derivatized) | splash10-000i-2920000000-1628d46d5520c5f20de8 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00dl-8910000000-78e8ee971ad7298c23cd | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00di-9200000000-805e6724e5181af78c81 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0006-0910000000-a212771a5ea868139d5a | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dl-9000000000-602d1e01bc7567493e4c | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00dl-9500000000-a758682a7aafbd0d553e | 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 (Non-derivatized) - 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 (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-9000000000-67498a3295a1fe788c4b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-9000000000-fb359f44fcf1b83ee14d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4i-9000000000-8e5f620c04615765a062 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014r-0900000000-619d80cc41221405e0bd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-9000000000-17ab53cec2e6b727c3e9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-9000000000-0dfbcc85d6423af91eda | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014l-4900000000-c50d79ba3a5013bcf29f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0uxr-0900000000-67a7784963ec75cecaa0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-9000000000-4569516f23d8a712b434 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-d928cac1226f19b8edc3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0900000000-34059351f2cbd94a8acc | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-a36d8d68a6705027415f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-014i-0900000000-1a5d8f4c1b293de18fed | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-014i-0900000000-b410df2c18dfc8ab7165 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0gi0-6900000000-c87ff036e3a5d15b7670 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-9000000000-561b3b28fa82e0b10658 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-05fr-9000000000-11e7c0a3d5cf8e4dedfe | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0a4i-9000000000-6a6f8cd9629b0f09469c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0a4i-9000000000-4518f691bbda5739c0f1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive | splash10-014i-0900000000-a931cfc8207edac33775 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-9000000000-430332b13b8c6368136b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-014i-0900000000-ffb286a8ae38a0a3e6d2 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00xr-9500000000-bb54662a5fd1dd142d90 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9000000000-1f7d9c10db4226a383c1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fu-9000000000-f6d7e45bb3f3436e5eb7 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-05fr-9000000000-5d10fb7acd70b2f43368 | JSpectraViewer | MoNA | 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 | 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 | 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: | - Martinez-Force, E., Benitez, T. (1995). "Effects of varying media, temperature, and growth rates on the intracellular concentrations of yeast amino acids." Biotechnol Prog 11:386-392.7654310
- UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- 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
- Ryan, E. D., Kohlhaw, G. B. (1974). "Subcellular localization of isoleucine-valine biosynthetic enzymes in yeast." J Bacteriol 120:631-637.4616942
- Hans, M. A., Heinzle, E., Wittmann, C. (2003). "Free intracellular amino acid pools during autonomous oscillations in Saccharomyces cerevisiae." Biotechnol Bioeng 82:143-151.12584756
- Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
- Dickinson, J. R., Harrison, S. J., Hewlins, M. J. (1998). "An investigation of the metabolism of valine to isobutyl alcohol in Saccharomyces cerevisiae." J Biol Chem 273:25751-25756.9748245
- 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: | Kinoshita, Shukuo; Udaka, Shigezo. L-Valine production by fermentation. (1962), 2 pp. |
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