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Key Documents

M1126

Sigma-Aldrich

L-Methionine sulfoxide

≥98% (TLC)

Synonym(s):

L-2-Amino-4-(methylsulfinyl)butanoic acid

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About This Item

Empirical Formula (Hill Notation):
C5H11NO3S
CAS Number:
Molecular Weight:
165.21
Beilstein:
4129939
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

Product Name

L-Methionine sulfoxide,

Assay

≥98% (TLC)

form

powder

color

white to off-white

mp

255 °C

application(s)

detection
peptide synthesis

SMILES string

CS(=O)CC[C@H](N)C(O)=O

InChI

1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10?/m0/s1

InChI key

QEFRNWWLZKMPFJ-YGVKFDHGSA-N

Gene Information

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Application

  • The DmsABC S-oxide reductase is an essential component of a novel, hypochlorite-inducible system of extracellular stress defense in Haemophilus influenzae: This study illustrates the enzymatic action of L-Methionine sulfoxide reductase in bacterial defense systems, underscoring its biotechnological applications in developing antimicrobial strategies (Nasreen et al., 2024).

Biochem/physiol Actions

L-Methionine sulfoxide, a structural analog of glutamate, may be used as a substrate to study the specificity and kinetics of various methionine sulfoxide reductase(s).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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Audrey S Vanhove et al.
PLoS pathogens, 13(6), e1006428-e1006428 (2017-06-07)
Vibrio cholerae is a diarrheal pathogen that induces accumulation of lipid droplets in enterocytes, leading to lethal infection of the model host Drosophila melanogaster. Through untargeted lipidomics, we provide evidence that this process is the product of a host phospholipid
Gabriel Javitt et al.
Antioxidants & redox signaling, 33(10), 665-678 (2020-06-11)
Aims: The post-translational oxidation of methionine to methionine sulfoxide (MetSO) is a reversible process, enabling the repair of oxidative damage to proteins and the use of sulfoxidation as a regulatory switch. MetSO reductases catalyze the stereospecific reduction of MetSO. One
Martina I Boxler et al.
Journal of proteome research, 16(9), 3310-3320 (2017-07-20)
3,4-Methylenedioxymethamphetamine (MDMA; "ecstasy") is widely consumed recreationally. Little is known about its effects on the human metabolome. Mapping biochemical changes after drug exposure can complement traditional approaches by revealing potential biomarkers of organ toxicity or discovering new metabolomic features in
Laura Wilk et al.
Journal of proteome research, 17(1), 600-617 (2017-11-22)
Streptococcus pyogenes is a major global health burden causing a wide variety of diseases. Because a vaccine against this bacterium is still lacking, vaccine candidates or antimicrobial therapies are urgently needed. Here we use an invasive and clinically relevant streptococcal
Eduardo Fuentes-Lemus et al.
Free radical biology & medicine, 152, 61-73 (2020-03-07)
Photosensitized protein oxidation is a promising tool for medical procedures such as photochemical tissue bonding (PTB). We have recently reported that the binding of rose Bengal, a sensitizer employed in PTB, to lysozyme modulates the photooxidation and crosslinking of this

Protocols

Separation of L-Methionine sulfone; L-Methionine sulfoximine; L-Methionine sulfoxide

Chromatograms

application for HPLC

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