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A4377

Sigma-Aldrich

S-(5′-Adenosyl)-L-methionine iodide

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

Synonym(s):

AdoMet, SAM

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About This Item

Empirical Formula (Hill Notation):
C15H23IN6O5S
CAS Number:
3493-13-8
Molecular Weight:
526.35
Beilstein/REAXYS Number:
4120787
EC Number:
222-486-5
MDL number:
MFCD00043192
UNSPSC Code:
12352209
PubChem Substance ID:
24890852
NACRES:
NA.26

Product Name

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

Quality Level

200

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

InChI key

XQMWYLXPEGFCFT-XKGORWRGSA-N

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Related Categories

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
GHS07

signalword

Warning

hcodes

H317

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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Certificates of Analysis (COA)

Lot/Batch Number
0000427051
0000427050
0000427049
0000427049
0000427051

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Noriyuki Onoue et al.
The Journal of biological chemistry, 286(17), 14903-14912 (2011-02-22)
Expression of the Arabidopsis CGS1 gene, encoding the first committed enzyme of methionine biosynthesis, is feedback-regulated in response to S-adenosyl-L-methionine (AdoMet) at the mRNA level. This regulation is first preceded by temporal arrest of CGS1 translation elongation at the Ser-94
Ernst G Malygin et al.
Critical reviews in biochemistry and molecular biology, 47(2), 97-193 (2012-01-21)
The sequence-specific transfer of methyl groups from donor S-adenosyl-L-methionine (AdoMet) to certain positions of DNA-adenine or -cytosine residues by DNA methyltransferases (MTases) is a major form of epigenetic modification. It is virtually ubiquitous, except for some notable exceptions. Site-specific methylation
Laura Gomez-Santos et al.
Methods in molecular biology (Clifton, N.J.), 826, 133-149 (2011-12-15)
S-Adenosylmethionine, abbreviated as SAM, SAMe or AdoMet, is the principal methyl group donor in the mammalian cell and the first step metabolite of the methionine cycle, being synthesized by MAT (methionine adenosyltransferase) from methionine and ATP. About 60 years after
Jianyu Zhang et al.
Journal of the American Chemical Society, 133(43), 17134-17137 (2011-10-01)
Human catechol-O-methyltransferase (COMT) catalyzes a methyl transfer from S-adenosylmethionine (AdoMet) to dopamine. Site-specific mutants at three positions (Tyr68, Trp38, and Val108) have been characterized with regard to product distribution, catalytic efficiency, and secondary kinetic isotope effects. The series of mutations
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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