(±)-Methionine
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(±)-Methionine

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(±)-Methionine is an essential amino acid involved in various biochemical processes in humans and mammals. It is also in poultry meal as a source of nutrition.

Category
DL-Amino Acids
Catalog number
BAT-008086
CAS number
59-51-8
Molecular Formula
C5H11NO2S
Molecular Weight
149.21
(±)-Methionine
IUPAC Name
2-amino-4-methylsulfanylbutanoic acid
Synonyms
DL-2-Amino-4-(methylthio)butyric acid
Appearance
White to off-white solid
Purity
>98%
Density
1.34 g/cm3
Melting Point
280°C (dec)
Boiling Point
306.9ºC at 760 mmHg
Storage
Store at RT
Solubility
Soluble in Aqueous Base
InChI
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
InChI Key
FFEARJCKVFRZRR-UHFFFAOYSA-N
Canonical SMILES
CSCCC(C(=O)O)N
1. The biological significance of methionine sulfoxide stereochemistry
Vadim N Gladyshev,Byung Cheon Lee Free Radic Biol Med . 2011 Jan 15;50(2):221-7. doi: 10.1016/j.freeradbiomed.2010.11.008.
Methionine can be oxidized by reactive oxygen species to a mixture of two diastereomers, methionine-S-sulfoxide and methionine-R-sulfoxide. Both free amino acid and protein-based forms of methionine-S-sulfoxide are stereospecifically reduced by MsrA, whereas the reduction of methionine-R-sulfoxide requires two enzymes, MsrB and fRMsr, which act on its protein-based and free amino acid forms, respectively. However, mammals lack fRMsr and are characterized by deficiency in the reduction of free methionine-R-sulfoxide. The biological significance of such biased reduction of methionine sulfoxide has not been fully explored. MsrA and MsrB activities decrease during aging, leading to accumulation of protein-based and free amino acid forms of methionine sulfoxide. Since methionine is an indispensible amino acid in human nutrition and a key metabolite in sulfur, methylation, and transsulfuration pathways, the consequences of accumulation of its oxidized forms require further studies. Finally, in addition to methionine, methylsulfinyl groups are present in various drugs and natural compounds, and their differential reduction by Msrs may have important therapeutic implications.
2. L-[Methyl- 11 C] Methionine-Positron-Emission Tomography (MET-PET)
Robert M Hoffman Methods Mol Biol . 2019;1866:267-271. doi: 10.1007/978-1-4939-8796-2_20.
Methionine (MET) dependence is a cancer-specific metabolic abnormality that is due to MET overuse for aberrant transmethylation reactions. [11C]-MET is very useful for positron-emission tomography (PET) due to MET overuse in malignant tumors. Many benefits of MET-PET have been demonstrated. MET-PET can differentiate recurrent glioma and necrosis. [11C]-MET-PET can also predict prognosis in gliomas better than [18F]-FDG PET. [11C]-MET-PET is better than MRI for predicting survival in low-grade glioma (LGG). MET-PET has greater specificity for detecting residual tumor after surgery than MRI.
3. Repurposing the Pummerer Rearrangement: Determination of Methionine Sulfoxides in Peptides
Joseph Ivanic,Rolf E Swenson,Carolyn C Woodroofe,Rodney L Levine,Sarah Monti Chembiochem . 2020 Feb 17;21(4):508-516. doi: 10.1002/cbic.201900463.
The reversible oxidation of methionine residues in proteins has emerged as a biologically important post-translational modification. However, detection and quantitation of methionine sulfoxide in proteins is difficult. Our aim is to develop a method for specifically derivatizing methionine sulfoxide residues. We report a Pummerer rearrangement of methionine sulfoxide treated sequentially with trimethylsilyl chloride and then 2-mercaptoimidazole or pyridine-2-thiol to produce a dithioacetal product. This derivative is stable to standard mass spectrometry conditions, and its formation identified oxidized methionine residues. The scope and requirements of dithioacetal formation are reported for methionine sulfoxide and model substrates. The reaction intermediates have been investigated by computational techniques and by13C NMR spectroscopy. These provide evidence for an α-chlorinated intermediate. The derivatization allows for detection and quantitation of methionine sulfoxide in proteins by mass spectrometry and potentially by immunochemical methods.
4. Methionine metabolism and methyltransferases in the regulation of aging and lifespan extension across species
Patrick Jouandin,Stephanie E Mohr,Andrey A Parkhitko,Norbert Perrimon Aging Cell . 2019 Dec;18(6):e13034. doi: 10.1111/acel.13034.
Methionine restriction (MetR) extends lifespan across different species and exerts beneficial effects on metabolic health and inflammatory responses. In contrast, certain cancer cells exhibit methionine auxotrophy that can be exploited for therapeutic treatment, as decreasing dietary methionine selectively suppresses tumor growth. Thus, MetR represents an intervention that can extend lifespan with a complementary effect of delaying tumor growth. Beyond its function in protein synthesis, methionine feeds into complex metabolic pathways including the methionine cycle, the transsulfuration pathway, and polyamine biosynthesis. Manipulation of each of these branches extends lifespan; however, the interplay between MetR and these branches during regulation of lifespan is not well understood. In addition, a potential mechanism linking the activity of methionine metabolism and lifespan is regulation of production of the methyl donor S-adenosylmethionine, which, after transferring its methyl group, is converted to S-adenosylhomocysteine. Methylation regulates a wide range of processes, including those thought to be responsible for lifespan extension by MetR. Although the exact mechanisms of lifespan extension by MetR or methionine metabolism reprogramming are unknown, it may act via reducing the rate of translation, modifying gene expression, inducing a hormetic response, modulating autophagy, or inducing mitochondrial function, antioxidant defense, or other metabolic processes. Here, we review the mechanisms of lifespan extension by MetR and different branches of methionine metabolism in different species and the potential for exploiting the regulation of methyltransferases to delay aging.
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