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Sigma-Aldrich

DL-Methionine

≥99.0% (NT)

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Synonym(s):
(±)-2-Amino-4-(methylmercapto)butyric acid, DL-2-Amino-4-(methylthio)butanoic acid
Linear Formula:
CH3SCH2CH2CH(NH2)COOH
CAS Number:
59-51-8
Molecular Weight:
149.21
Beilstein:
636185
EC Number:
200-432-1
MDL number:
MFCD00063096
PubChem Substance ID:
329759959
NACRES:
NA.26

Quality Level

200

Assay

≥99.0% (NT)

form

powder or crystals

optical activity

[α]/D, c = 5 in 5 M HCl (inactive)

concentration

5% in 5 M HCl

ign. residue

≤0.05%

color

white

mp

280 °C (dec.) (lit.)

solubility

5 M HCl: 1 g/10 mL, clear, colorless to almost colorless

suitability

corresponds for TLC

application(s)

peptide synthesis

SMILES string

CSCCC(N)C(O)=O

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

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Application

DL-Methionine has been used to study the susceptibility of methionine to oxidation during the development of monoclonal antibodies.

Biochem/physiol Actions

Methionine is an essential amino acid which acts a precursor for transmethylation and transsulfuration. In proteins, L-methionine is the biologically active form. D-methionine is converted to L-methionine by enzymes in the body. 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Rapid assessment of oxidation via middle-down LCMS correlates with methionine side-chain solvent-accessible surface area for 121 clinical stage monoclonal antibodies
Rong Yang
MAbs (2017)
L-methionine as immune supportive supplement: a clinical evaluation.
Van Brummelen and du Toit D
Amino Acids, 33(1), 157-163 (2007)
Bio-Methionine Production from Glucose - Cost Analysis - Methionine E31A (2016)
Il Jin Cho et al.
Biochemical and biophysical research communications, 367(1), 190-194 (2008-01-02)
We investigated the hypolipidemic effect of resveratrol focused on the mRNA expression and hepatic HMG-CoA reductase (HMGR) activity in hamsters fed a high-fat diet. Male Syrian Golden hamsters were fed a high-fat diet containing 0.025% fenofibrate or 0.025% resveratrol for
Pilar Lloris-Garcerá et al.
Journal of molecular biology, 426(11), 2246-2254 (2014-04-03)
The increasing number of solved membrane protein structures has led to the recognition of a common feature in a large fraction of the small-molecule transporters: inverted repeat structures, formed by two fused homologous membrane domains with opposite orientation in the
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