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Merck

A4377

Sigma-Aldrich

S-(5′-Adenosyl)-L-methionine iodide

≥80% (spectrophotometric assay), suitable for cell culture

Sinónimos:

AdoMet, SAM

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About This Item

Fórmula empírica (notación de Hill):
C15H23IN6O5S
Número de CAS:
Peso molecular:
526.35
Beilstein/REAXYS Number:
4120787
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

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product name

S-(5′-Adenosyl)-L-methionine iodide, ≥80% (HPLC), ≥80% (spectrophotometric assay)

assay

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

form

powder

technique(s)

cell culture | mammalian: suitable

color

white to off-white

solubility

H2O: 100 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

[I-].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.HI/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);1H/t7-,8+,10+,11+,14+,27?;/m0./s1

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Application

S-(5′-Adenosyl)-L-methionine (SAM, AdoMet) is used as a primary methyl donor molecule in mammalian cell culture and the first step metabolite in methionine biosynthesis.

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 very unstable at room temperature.

Analysis Note

Purity based on UV and HPLC.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)


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T Kakutani et al.
Nucleic acids research, 23(1), 130-137 (1995-01-11)
We have recently isolated two Arabidopsis thaliana DNA hypomethylation mutations, identifying the DDM1 locus, that cause a 70% reduction in genomic 5-methylcytosine levels [1]. Here we describe further phenotypic and biochemical characterization of the ddm1 mutants. ddm1/ddm1 homozygotes exhibited altered
Soon Goo Lee et al.
The Journal of biological chemistry, 287(2), 1426-1434 (2011-11-26)
In the malarial parasite Plasmodium falciparum, a multifunctional phosphoethanolamine methyltransferase (PfPMT) catalyzes the methylation of phosphoethanolamine (pEA) to phosphocholine for membrane biogenesis. This pathway is also found in plant and nematodes, but PMT from these organisms use multiple methyltransferase domains
Benjamin R Duffus et al.
Biochimica et biophysica acta, 1824(11), 1254-1263 (2012-01-25)
Radical S-adenosylmethionine (AdoMet) enzymes comprise a large superfamily of proteins that engage in a diverse series of biochemical transformations through generation of the highly reactive 5'-deoxyadenosyl radical intermediate. Recent advances into the biosynthesis of unique iron-sulfur (FeS)-containing cofactors such as
Yui Yamashita et al.
The Journal of biological chemistry, 289(18), 12693-12704 (2014-03-22)
Expression of CGS1, which codes for an enzyme of methionine biosynthesis, is feedback-regulated by mRNA degradation in response to S-adenosyl-L-methionine (AdoMet). In vitro studies revealed that AdoMet induces translation arrest at Ser-94, upon which several ribosomes stack behind the arrested
Renata Z Jurkowska et al.
Methods in molecular biology (Clifton, N.J.), 791, 157-177 (2011-09-14)
DNA methyltransferases are important enzymes and their inhibition has many potential applications. The investigation of DNA methyltransferases as well as screening for potential inhibitors requires specialized enzyme assays. In this chapter, we describe three DNA methyltransferase assays, each of them

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