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M6626

Sigma-Aldrich

S-Methyl-L-cysteine

suitable for ligand binding assays

Synonyme(s) :

(R)-2-Amino-3-(methylmercapto)propionic acid, SMLC

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About This Item

Formule linéaire :
CH3SCH2CH(NH2)CO2H
Numéro CAS:
Poids moléculaire :
135.18
Numéro Beilstein :
1721675
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
Nomenclature NACRES :
NA.26

product name

S-Methyl-L-cysteine, substrate for methionine sulfoxide reductase A

Niveau de qualité

Forme

powder

Technique(s)

ligand binding assay: suitable

Application(s)

peptide synthesis

Température de stockage

−20°C

Chaîne SMILES 

CSC[C@H](N)C(O)=O

InChI

1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

Clé InChI

IDIDJDIHTAOVLG-VKHMYHEASA-N

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Application


  • In-vitro antioxidant and anti-inflammatory potential along with p.o. pharmacokinetic profile of key bioactive phytocompounds of Snow Mountain Garlic: a comparative analysis vis-à-vis normal garlic.: This study examines the antioxidant and anti-inflammatory properties of S-Methyl-L-cysteine found in Snow Mountain Garlic, providing insights into its potential therapeutic applications (Kaur et al., 2024).

  • Acidification and tissue disruption affect glucosinolate and S-methyl-l-cysteine sulfoxide hydrolysis and formation of amines, isothiocyanates and other organosulfur compounds in red cabbage (Brassica oleracea var. capitata f. rubra).: The research highlights how acidification and tissue disruption influence the hydrolysis of S-Methyl-L-cysteine sulfoxide, impacting the formation of various bioactive compounds in red cabbage (Hanschen, 2024).

  • Selective cycloaddition of ethylene oxide to CO(2) within the confined space of an amino acid-based metal-organic framework.: This research explores the use of an S-Methyl-L-cysteine-based metal-organic framework for the selective cycloaddition of ethylene oxide to CO2, demonstrating its potential in green chemistry and materials science (Bilanin et al., 2023).

Actions biochimiques/physiologiques

S-Methyl-L-cysteine (SMLC) is a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA). SMLC is naturally present in garlic, cabbage, and turnips and has been studied as a theurapeutic for neurodegenerative diseases including Parkinson′s.
When used as a dietary supplement in the Drosphilia model of PD, SMLC increases the efficacy of the MRSA catalytic antioxidant system by providing additional substrate available leading to increased resistance to oxidative stress.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Maximilian J Helf et al.
Chembiochem : a European journal of chemical biology, 18(5), 444-450 (2016-12-15)
Amino acid modifications are essential for the structural diversity and bioactivity of ribosomally synthesized and post-translationally modified peptide natural products (RiPPs). A particularly large and virtually untapped pool of unusual RiPPs and associated modifying enzymes is provided by uncultivated bacteria.
Thambi Dorai et al.
Biomolecules, 10(1) (2019-12-22)
Abstract: Many tumors readily convert l-glutamine to α-ketoglutarate. This conversion is almost invariably described as involving deamidation of l-glutamine to l-glutamate followed by a transaminase (or dehydrogenase) reaction. However, mammalian tissues possess another pathway for conversion of l-glutamine to α-ketoglutarate
Methionine sulfoxide reductase A and a dietary supplement S-methyl-L-cysteine prevent Parkinson's-like symptoms.
Wassef, R. et al.
The Journal of Neuroscience, 21, 12808-12816 (2007)
Ramez Wassef et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 27(47), 12808-12816 (2007-11-23)
Parkinson's disease (PD), a common neurodegenerative disease, is caused by loss of dopaminergic neurons in the substantia nigra. Although the underlying cause of the neuronal loss is unknown, oxidative stress is thought to play a major role in the pathogenesis
Cheng-chin Hsu et al.
The Journal of nutrition, 134(1), 149-152 (2004-01-06)
Balb/cA mice were used to study the in vivo effect of N-acetyl cysteine, S-allyl cysteine, S-ethyl cysteine, S-methyl cysteine and S-propyl cysteine, all derived from garlic, on glutathione (GSH) concentration and catalase and glutathione peroxidase (GPX) activities in plasma, kidney

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