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| Identification |
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| YMDB ID | YMDB00318 |
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| Name | L-Methionine |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Methionine (abbreviated as Met or M) 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 amino acid, because of the hydrophobic nature of the thioether-alkyl side chain. Together with cysteine, methionine is one of two sulfur-containing proteinogenic amino acids. Its derivative S-adenosyl methionine (SAM) serves as a methyl donor. Methionine is an intermediate in the biosynthesis of cysteine, carnitine, taurine, lecithin, phosphatidylcholine, and other phospholipids. Methionine is synthesized via a pathway that uses both aspartic acid and cysteine. First, aspartic acid is converted via β-aspartyl-semialdehyde into homoserine, introducing the pair of contiguous methylene groups. Homoserine converts to O-succinyl homoserine, which then reacts with cysteine to produce cystathionine, which is cleaved to yield homocysteine. Subsequent methylation of the thiol group by folates affords methionine. The principal fates methionine are incorporation into polypeptide chains, and use in the production of alpha-ketobutyrate and cysteine via SAM (S-adenosylmethionine). The transulfuration reactions that produce cysteine from homocysteine and serine also produce alpha-ketobutyrate, the latter being converted first to propionyl-CoA and then via a 3-step process to succinyl-CoA. |
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| Structure | |
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| Synonyms | - (2S)-2-amino-4-(methylsulfanyl)butanoate
- (2S)-2-amino-4-(methylsulfanyl)butanoic acid
- (l)-methionine
- (s)-(+)-methionine
- (S)-2-amino-4-(methylthio)-Butanoate
- (S)-2-amino-4-(methylthio)-Butanoic acid
- (S)-2-Amino-4-(methylthio)butanoate
- (S)-2-Amino-4-(methylthio)butanoic acid
- (S)-2-amino-4-(methylthio)butyric acid
- (s)-methionine
- 2-Amino-4-(methylthio)butyrate
- 2-Amino-4-(methylthio)butyric acid
- 2-Amino-4-methylthiobutanoate
- 2-Amino-4-methylthiobutanoic acid
- A-amino-g-methylmercaptobutyrate
- A-amino-g-methylmercaptobutyric acid
- Acimethin
- alpha-amino-alpha-aminobutyric acid
- alpha-amino-gamma-methylmercaptobutyrate
- Alpha-amino-gamma-methylmercaptobutyric acid
- Cymethion
- G-methylthio-a-aminobutyrate
- G-methylthio-a-aminobutyric acid
- gamma-methylthio-alpha-aminobutyrate
- gamma-methylthio-alpha-aminobutyric acid
- H-met-h
- H-met-oh
- L-(-)-methionine
- l-2-Amino-4-(methylthio)butyric acid
- L-2-Amino-4methylthiobutyric acid
- L-a-amino-g-methylthiobutyrate
- L-a-amino-g-methylthiobutyric acid
- L-alpha-amino-gamma-methylmercaptobutyric acid
- L-alpha-amino-gamma-methylthiobutyrate
- L-alpha-amino-gamma-methylthiobutyric acid
- L-gamma-methylthio-alpha-aminobutyric acid
- L-methionin
- L-Methionine
- L-methioninum
- L(-)-amino-alpha-amino-alpha-aminobutyric acid
- L(-)-amino-gamma-methylthiobutyric acid
- Liquimeth
- Mepron
- MET
- Methilanin
- Methionine
- Methioninum
- Metionina
- Neo-methidin
- Poly-l-methionine
- Polymethionine
- S-methionine
- S-methyl-l-homocysteine
- M
- L-Methionine Z
- (2S)-2-Amino-4-(methylsulphanyl)butanoate
- (2S)-2-Amino-4-(methylsulphanyl)butanoic acid
- (S)-2-Amino-4-(methylthio)butyrate
- L-a-Amino-g-methylmercaptobutyrate
- L-a-Amino-g-methylmercaptobutyric acid
- L-alpha-Amino-gamma-methylmercaptobutyrate
- L-Α-amino-γ-methylmercaptobutyrate
- L-Α-amino-γ-methylmercaptobutyric acid
- L-2-Amino-4methylthiobutyrate
- L-2-Amino-4-methylthiobutyric acid
- Toxin war
- L-Isomer methionine
- Methionine, L-isomer
- Pedameth
- Methionine, L isomer
- (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol
- Bo-xan
- e 161b
- Xanthophyll
- (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol
- (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol
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| CAS number | 63-68-3 |
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| Weight | Average: 149.211
Monoisotopic: 149.051049291 |
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| InChI Key | FFEARJCKVFRZRR-BYPYZUCNSA-N |
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| InChI | InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 |
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| IUPAC Name | (2S)-2-amino-4-(methylsulfanyl)butanoic acid |
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| Traditional IUPAC Name | L-methionine |
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| Chemical Formula | C5H11NO2S |
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| SMILES | [H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])SC([H])([H])[H] |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine 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 | Methionine and derivatives |
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| Alternative Parents | |
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| Substituents | - Methionine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Thia fatty acid
- Fatty acid
- Fatty acyl
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Thioether
- Sulfenyl compound
- Dialkylthioether
- Amine
- Organic oxygen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Organopnictogen compound
- Organic oxide
- 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 | 284 °C |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | 56.6 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | | LogP | -1.87 [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 | Not Available |
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| SMPDB Pathways | |
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| KEGG Pathways | |
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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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| 344 ± 7 µM | YPD media | aerobic | Baker's yeast | PMID: 7654310 | | 344 ± 7 µM | YPG media | aerobic | Baker's yeast | PMID: 7654310 | | 69 ± 1 µM | SD media | aerobic | Baker's yeast | PMID: 7654310 | | 69 ± 1 µM | SG media | aerobic | Baker's yeast | PMID: 7654310 | | 275 ± 5 µM | M (molasses) | aerobic | Baker's yeast | PMID: 7654310 | | 137 ± 3 µM | MA (molasses) | aerobic | Baker's yeast | PMID: 7654310 | | 69 ± 1 µM | MB (molasses) | aerobic | Baker's yeast | PMID: 7654310 | | 137 ± 3 µM | MAB (molasses) | aerobic | Baker's yeast | PMID: 7654310 | | 592 ± 30 µM | YEB media with 0.5 mM glucose | aerobic | Baker's yeast | Experimentally Determined
Not Available | | 160 ± 34 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) | splash10-004i-0920000000-945c85aa7c9f5eb2dfbb | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-004i-0910000000-b837ee0f4413856560f1 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00b9-7910000000-5a1558fbb2f5e86edc9b | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0udi-1900000000-1a97567ce4f25c4e8263 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-004i-0910000000-1b0477118cb20549bf4d | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-0920000000-8ffae5d87508e0704903 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0920000000-945c85aa7c9f5eb2dfbb | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0910000000-b837ee0f4413856560f1 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-QQ (Non-derivatized) | splash10-01bc-2692000000-c6a4af434abaeea2de87 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00b9-7910000000-5a1558fbb2f5e86edc9b | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-1900000000-1a97567ce4f25c4e8263 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004i-0910000000-1b0477118cb20549bf4d | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0mbd-9200000000-77e5cfb78936ad02d71c | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9510000000-c03dec8575710eed861e | 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) | splash10-0uea-1900000000-b991859b2c5bed6592a8 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-08fr-9000000000-66855ace60e59837f131 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-08fr-9000000000-56a567791c824c6a9da6 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0fe0-0900000000-d680295f21b2e2b40366 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-062d3540db4db22da836 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-84467513e2c9ec1a6851 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-88dc2bebb198eea550ef | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0920000000-b444ad79abeb16acde43 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-6e24a8df417e5f3db58c | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-c60ef880eb9a816a274b | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-a7b7d1a3481c0c691a5b | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0002-0900000000-9156f088f4cc9eafa892 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0002-9200000000-f78ba2aab8d5a0e0b135 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0002-9000000000-e7b819fd2d0ac3862860 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0002-9000000000-b61396e720381bd5ff85 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0002-9000000000-b61396e720381bd5ff85 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0udi-0900000000-c3557cb41fd6fe268819 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0udi-6900000000-6bf5af2d1c561013948a | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-08fr-9000000000-63c9b1c138f9a27490e5 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-03di-9000000000-e133c47b0efe4992589f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-03di-9000000000-dee78b4f34f8732fedb0 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive | splash10-0udi-0900000000-d3f03ff5e8eacc8b6c8e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0900000000-e0dd5ff44b7962f6a2d2 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-2900000000-305916dde72c899993b6 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-9800000000-47e0a34a2ec02bd762bf | 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 | 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 | 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
- White, W. H., Gunyuzlu, P. L., Toyn, J. H. (2001). "Saccharomyces cerevisiae is capable of de Novo pantothenic acid biosynthesis involving a novel pathway of beta-alanine production from spermine." J Biol Chem 276:10794-10800.11154694
- Cherest, H., Eichler, F., Robichon-Szulmajster, H. (1969). "Genetic and regulatory aspects of methionine biosynthesis in Saccharomyces cerevisiae." J Bacteriol 97:328-336.5764336
- Pirkov, I., Norbeck, J., Gustafsson, L., Albers, E. (2008). "A complete inventory of all enzymes in the eukaryotic methionine salvage pathway." FEBS J 275:4111-4120.18625006
- 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
- Mulet, J. M., Alemany, B., Ros, R., Calvete, J. J., Serrano, R. (2004). "Expression of a plant serine O-acetyltransferase in Saccharomyces cerevisiae confers osmotic tolerance and creates an alternative pathway for cysteine biosynthesis." Yeast 21:303-312.15042590
- Chiang, P. K., Cantoni, G. L. (1977). "Activation of methionine for transmethylation. Purification of the S-adenosylmethionine synthetase of bakers' yeast and its separation into two forms." J Biol Chem 252:4506-4513.194884
- 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
- Suliman, H. S., Sawyer, G. M., Appling, D. R., Robertus, J. D. (2005). "Purification and properties of cobalamin-independent methionine synthase from Candida albicans and Saccharomyces cerevisiae." Arch Biochem Biophys 441:56-63.16083849
- Thomas, D., Becker, A., Surdin-Kerjan, Y. (2000). "Reverse methionine biosynthesis from S-adenosylmethionine in eukaryotic cells." J Biol Chem 275:40718-40724.11013242
- Csaikl, U., Csaikl, F. (1986). "Molecular cloning and characterization of the MET6 gene of Saccharomyces cerevisiae." Gene 46:207-214.3542720
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| Synthesis Reference: | Boy, Matthias; Klein, Daniela; Schroeder, Hartwig. Method for the production and recovery of methionine. PCT Int. Appl. (2005), 34 pp. |
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| External Links: | |
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