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A4377

S-(5′-Adenosyl)-L-methionine iodide

Name: S-(5&#8242;-Adenosyl)-<SC>L</SC>-methionine iodide
Brand: SIGMA

≥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

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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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

Related Categories

Biochemicals

Cell Culture Supplements & Reagents

Amino Acids – Building Blocks of Life Science

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.

Analysis Note

Purity based on UV and HPLC.

Disclaimer

This material is very unstable at room temperature.

pictograms

GHS07

signalword

Warning

hcodes

H317

pcodes

P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364

Hazard Classifications

Skin Sens. 1

Storage Class

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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SAMe and HuR in liver physiology: usefulness of stem cells in hepatic differentiation research.

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

DNA methyltransferases: mechanistic models derived from kinetic analysis.

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

Enzymatic methyl transfer: role of an active site residue in generating active site compaction that correlates with catalytic efficiency.

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

Structure and reaction mechanism of phosphoethanolamine methyltransferase from the malaria parasite Plasmodium falciparum: an antiparasitic drug target.

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

Characterization of an Arabidopsis thaliana DNA hypomethylation mutant.

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

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Global Trade Item Number

SKU	GTIN
A4377-25MG	04061833368817
A4377-5MG	04061833369142
A4377-100MG	04061833368770

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