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A7007 Sigma-Aldrich

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

≥75%

Synonym: Active methionine, AdoMet, SAM chloride dihydrochloride

  • CAS Number 86867-01-8

  • Empirical Formula (Hill Notation) C15H23ClN6O5S · 2 HCl

  • Molecular Weight 507.82

  •  Beilstein/REAXYS Number 6560002

  •  MDL number MFCD22571809

  •  PubChem Substance ID 24891164

  •  NACRES NA.32

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Properties

Related Categories Biochemicals and Reagents, Cancer Research, Cell Biology, Chemopreventive Agents, Coenzymes and Cofactors,
Quality Level   200
assay   ≥75%
form   powder
application(s)   cell analysis: suitable
color   white to off-white
solubility   H2O: 100 mg/mL
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

Description

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.

Packaging

1 g in poly bottle

25, 100, 500 mg in poly bottle

5 mg in glass bottle

Biochem/physiol Actions

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.

Caution

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.

Analysis Note

Purity based on UV and HPLC.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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