A7007

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

≥75%

• Synonym(s): SAM, Active methionine, AdoMet, SAM chloride dihydrochloride
• Empirical Formula (Hill Notation): C₁₅H₂₃ClN₆O₅S · 2 HCl
• CAS Number: 86867-01-8
• Molecular Weight: 507.82
• Beilstein/REAXYS Number: 6560002
• MDL number: MFCD22571809
• UNSPSC Code: 12352209
• PubChem Substance ID: 24891164
• NACRES: NA.32

Properties

• biological source: synthetic (chemical)
• Quality Level: 300
• 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

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.

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 Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable