A7007
S-(5′-Adenosyl)-L-methionine chloride dihydrochloride
≥75%
Synonyme(s) :
SAM, Active methionine, AdoMet, SAM chloride dihydrochloride
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A propos de cet article
Formule empirique (notation de Hill) :
C15H23ClN6O5S · 2 HCl
Numéro CAS:
Poids moléculaire :
507.82
UNSPSC Code:
12352209
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
6560002
Form:
powder
Assay:
≥75%
Solubility:
H2O: 100 mg/mL
Biological source:
synthetic (chemical)
Color:
white to off-white
Service technique
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synthetic (chemical)
Quality Level
assay
≥75%
form
powder
color
white to off-white
solubility
H2O: 100 mg/mL
application(s)
cell analysis
shipped in
dry ice
storage temp.
−20°C
SMILES string
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
InChI key
KBAFOJZCBYWKPU-XQVUROGGSA-N
General description
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.
Biochem/physiol Actions
Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT).
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.
Analysis Note
Purity based on UV and HPLC.
Disclaimer
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.
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
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
Membrane bound COMT isoform is an interfacial enzyme: general mechanism and new drug design paradigm
Magarkar A, et al.
Chemical Communications (Cambridge, England), 54(28), 3440-3443 (2018)