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A2408

Sigma-Aldrich

S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt

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

Synonym(s):

AdoMet, SAM p-toluenesulfonate salt

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About This Item

Empirical Formula (Hill Notation):
C15H23N6O5S · C7H7O3S · xC7H8O3S
CAS Number:
52248-03-0
Molecular Weight:
570.64 (free base basis)
UNSPSC Code:
12352209
PubChem Substance ID:
24890653
NACRES:
NA.32

biological source

synthetic (Organic)

Quality Level

300

assay

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

form

powder

composition

p-Toluenesulfonate content, 1.6-4.4 mol/mol

color

white to off-white

solubility

H2O: 100 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(O[H])[C@](N([H])[H])([H])C([H])([H])C([H])([H])[S@+](C([H])([H])[H])C([H])([H])[C@@]([C@](O[H])([H])[C@@]1([H])O[H])([H])O[C@]1([H])N2C3=C(N=C2[H])C(N([H])[H])=NC([H])=N3.O=S(C4=C([H])C([H])=C(C([H])([H])[H])C([H])=C4[H])([O-])=O

InChI

1S/C15H22N6O5S.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);2-5H,1H3,(H,8,9,10)/t7-,8+,10+,11+,14+,27?;/m0./s1

InChI key

VHPOFDUCFKOUHV-XKGORWRGSA-N

Related Categories

General description

S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt is used for the treatment of depression, liver cirrhosis, cholestasis and degenerative joint disease.

Application

S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt has been used for cell proliferation assay. It has also been used for methylation assay.

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.
S-(5′-Adenosyl)-L-methionine (SAM) is anti-apoptotic in normal hepatocytes and normal colon epithelial cells but pro-apoptotic in liver human hepatocellular carcinoma (HCC), HepG2 cells and colon cancer cells.

Caution

This material is unstable at room temperature.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Allison B Norvil et al.
Nucleic acids research, 48(7), 3761-3775 (2020-03-04)
We have previously shown that the highly prevalent acute myeloid leukemia (AML) mutation, Arg882His, in DNMT3A disrupts its cooperative mechanism and leads to reduced enzymatic activity, thus explaining the genomic hypomethylation in AML cells. However, the underlying cause of the
Le Thanh Mai Pham et al.
Enzyme and microbial technology, 82, 66-73 (2015-12-18)
Using bioinformatic homology search tools, this study utilized sequence phylogeny, gene organization and conserved motifs to identify members of the family of O-methyltransferases from lignin-degrading fungus Phanerochaete chrysosporium. The heterologous expression and characterization of O-methyltransferases from P. chrysosporium were studied.
Lupus autoimmunity altered by cellular methylation metabolism
Yang ML, et al.
Autoimmunity, 46(1), 21-31 (2013)
Dietary supplement S-adenosyl-L-methionine (AdoMet) effects on plasma homocysteine levels in healthy human subjects: a double-blind, placebo-controlled, randomized clinical trial
Thompson MA, et al.
Journal of Alternative and Complementary Medicine (New York, N.Y.), 15(5), 523-529 (2009)
Yang-Liu Xia et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1157, 122333-122333 (2020-09-01)
Catechol-O-methyltransferase (COMT) is a major drug metabolizing enzyme in humans. COMT expression is directedly associated with various mental diseases and cancers due to its essential role in catalyzing metabolic inactivation of endogenous catecholamines and catechol estrogens. However, a practical method
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