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Key Documents

A7007

Sigma-Aldrich

S-(5′-Adenosyl)-L-methionine chloride dihydrochloride

≥75%

Synonyme(s) :

SAM, Active methionine, AdoMet, SAM chloride dihydrochloride

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About This Item

Formule empirique (notation de Hill):
C15H23ClN6O5S · 2 HCl
Numéro CAS:
Poids moléculaire :
507.82
Numéro Beilstein :
6560002
Numéro MDL:
Code UNSPSC :
12352209
ID de substance PubChem :
Nomenclature NACRES :
NA.32

Niveau de qualité

Pureté

≥75%

Forme

powder

Couleur

white to off-white

Solubilité

H2O: 100 mg/mL

Application(s)

cell analysis

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

Cl.Cl.[Cl-].C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23

InChI

1S/C15H22N6O5S.3ClH/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21;;;/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);3*1H/t7-,8+,10+,11+,14+,27?;;;/m0.../s1

Clé InChI

KBAFOJZCBYWKPU-XQVUROGGSA-N

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Description générale

S-(5′-Adenosyl)-L-methionine chloride dihydrochloride (SAM) facilitates the transfer of methyl groups to proteins, lipids and nucleic acids. Methionine adenosyl transferase catalyses the synthesis of SAM from methionine and adenosine triphosphate (ATP). SAM functions to regulate various cellular functions like cell division, cell death, transcription, genetic stability, oxidant/antioxidant balance and polyamine homeostasis. Therapeutically, SAM finds its application as a nutritional supplement in humans for various diseases like osteoarthritis and liver injury. SAM also regulates transsulfuration reactions by binding to the regulatory domain of key enzyme cystathionine-β-synthase (CBS).

Application

S-(5′-Adenosyl)-L-methionine chloride dihydrochloride has been used as a medium supplement for S30 cell extract. It also has been used for measuring the interaction with catechol-O-methyltransferase (COMT) by quartz crystal microbalance (QCM), surface plasmon resonance (SPR) and isothermal titration calorimetry (ITC) with supported lipid bilayers and vesicles.

Actions biochimiques/physiologiques

Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also involved in regulating liver function, growth, and response to injury.

Attention

This material is 80-90% pure when prepared, but is very unstable. As much as 10% purity loss per day at 25 °C has been noted.

Remarque sur l'analyse

Purity based on UV and HPLC.

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


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Consulter la Bibliothèque de documents

Leah C Beauchamp et al.
Journal of Alzheimer's disease : JAD, 77(4), 1705-1715 (2020-09-15)
Alterations in the methionine cycle and abnormal tau phosphorylation are implicated in many neurodegenerative diseases, including Alzheimer's disease and frontotemporal dementia. rTg4510 mice express mutant human P301L tau and are a model of tau hyperphosphorylation. The cognitive deficit seen in
Chemical communication between bacteria and cell-free gene expression systems within linear chains of emulsion droplets
Schwarz-Schilling M, et al.
Integrative Biology : Quantitative Biosciences from Nano to Macro, 8(4), 564-570 (2016)
Yan Zhang et al.
Archives of microbiology, 191(10), 773-783 (2009-09-05)
Enolase-phosphatase (E1), as an enzyme, is involved in methionine salvage pathway in many prokaryotic and eukaryotic organisms. But the identity and function of E1 in Xanthomonas oryzae pv. oryzae (Xoo) remain undetermined. Here, we report the cloning and characterization of
Andria V Rodrigues et al.
Chembiochem : a European journal of chemical biology, 21(5), 663-671 (2019-09-13)
We recently reported the discovery of phenylacetate decarboxylase (PhdB), representing one of only ten glycyl-radical-enzyme reaction types known, and a promising biotechnological tool for first-time biochemical synthesis of toluene from renewable resources. Here, we used experimental and computational data to
Ted M Lakowski et al.
Analytical biochemistry, 396(1), 158-160 (2009-09-08)
S-Adenosyl-L-homocysteine (AdoHcy) background signal in reactions with protein arginine N-methyltransferase 1 is investigated using an ultrahigh-performance liquid chromatography tandem mass spectrometry assay that measures AdoHcy. We identify three sources of AdoHcy background: enzymatic automethylation, AdoHcy contamination in commercial S-adenosyl-L-methionine (AdoMet)

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