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Merck

A4377

S-(5′-Adenosyl)-L-methionine iodide

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

Sinónimos:

AdoMet, SAM

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Fórmula empírica (notación de Hill):
C15H23IN6O5S
Número CAS:
3493-13-8
Peso molecular:
526.35
NACRES:
NA.26
PubChem Substance ID:
24890852
UNSPSC Code:
12352209
EC Number:
222-486-5
MDL number:
MFCD00043192
Beilstein/REAXYS Number:
4120787

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Nombre del producto

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

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

InChI key

XQMWYLXPEGFCFT-XKGORWRGSA-N

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

Quality Level

200

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Analysis Note

Purity based on UV and HPLC.

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.

Disclaimer

This material is very unstable at room temperature.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000488961
0000488962
0000488963
0000488963
0000488962

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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
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
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
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