Synonyms
(S)-2-Amino-4-(methylmercapto)butyric acid, L-2-Amino-4-(methylthio)butanoic acid
IUPAC Name
(2S)-2-Amino-4-methylsulfanylbutanoic acid
Molecular Formula
CH3SCH2CH2CH(NH2)CO2H
Canonical SMILES
CSCC[C@H](N)C(O)=O
InChI
1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
InChI Key
FFEARJCKVFRZRR-BYPYZUCNSA-N
Melting Point
284 ℃(dec.) (lit.)
Application
L-Methionine has been used as a component of media to culture various cancer cells and to study its effects on the cell cycle. It has also been used as a component of DMEM medium to culture satellite cells from the white muscle of trouts.
Biochem Physiol Actions
Methionine is an essential amino acid which acts a precursor for transmethylation and transsulphuration. In proteins, L-methionine is the biologically active form. The adenosylation of methionine results in the formation of S-adenosyl-L-methionine (SAM), which serves as a methyl donor to various substances. L-Methionine's metabolic product glutathione is known to regulate immune response and has antiviral action.
Biological Source
non-animal source
Color/Form
Minute hexagonal plates from dilute alcohol;Colorless or white, lustrous plates or as white, crystalline powder;
Covalently-Bonded Unit Count
1
Decomposition
When heated to decomposition it emits very toxic fumes of /nitric oxide/ and /sulfur oxide/.;
Defined Atom Stereocenter Count
1
Gene Information
rat Ggt1(116568)
Impurities
endotoxin, tested
Isomeric SMILES
CSCC[C@@H](C(=O)O)N
Monoisotopic Mass
149.05104977
Octanol Water Partition Coefficient
-1.87 (LogP);log Kow = -1.87;-1.87;
Other Experimental
Specific optical rotation: +8.12 deg at 25 deg C/D (c = 0.8); -21.19 deg at 25 deg C/D (c = 0.8 in 0.2N HCl) /Methione, D-form/;Platelets from alcohol. mp 281 deg C (decomposes), density 1.340; pKa1 = 2.28, pKa2 = 9.21; pH of 1% aqueous solution 5.6-6.1; Rf value 0.77. Solubility in water (g/L) at 0 deg C: 18.18; at 25 deg C: 33.81; at 50 deg C: 60/.70; at 75 deg C: 15.2 deg C. Soluble in dilute acids, alkalies. Very slightly soluble in 95% alcohol. Insoluble in ether. /Methionine, DL-form/;IR: 2549 (Coblentz Society Spectral Collection) /Methionine (DL)/;UV: 1-65 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Methionine (DL)/;13C NMR: 135 (Johnson and Jankowski, Carbon-13 NMR Spectra, John Wiley & Sons, New York) /Methionine (DL)/;MASS: 442 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63) /Methionine (DL)/;Henry's Law constant = 2.11X10-11 atm-cu m/mol at 25 deg C (est);Hydroxyl radical reaction rate constant = 5.13X10-11 cu cm/molec-sec at 25 deg C (est);
Physical Description
Minute hexagonal plates from dilute alcohol. (NTP, 1992);Solid;
Technique
cell culture | mammalian: suitable
Topological Polar Surface Area
88.6 Ų
Undefined Atom Stereocenter Count
1
Vapor Pressure
8.14X10-8 mm Hg at 25 deg C (est);
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