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A7007

Sigma-Aldrich

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

≥75%

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Synonym(s):
SAM, Active methionine, AdoMet, SAM chloride dihydrochloride
Empirical Formula (Hill Notation):
C15H23ClN6O5S · 2 HCl
CAS Number:
Molecular Weight:
507.82
Beilstein:
6560002
MDL number:
PubChem Substance ID:
NACRES:
NA.32

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

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1 of 4

This Item
A2408798231A9384
vibrant-m

A9384

S-(5′-Adenosyl)-L-homocysteine

assay

≥75%

assay

≥80% (HPLC), ≥80% (spectrophotometric assay)

assay

≥90% (CP)

assay

≥98.0% (HPLC), ≥98.0% (TLC)

solubility

H2O: 100 mg/mL

solubility

H2O: 100 mg/mL

solubility

-

solubility

1 M HCl: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow

shipped in

dry ice

shipped in

dry ice

shipped in

-

shipped in

-

color

white to off-white

color

white to off-white

color

-

color

-

form

powder

form

powder

form

solid

form

crystalline

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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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