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A9384 Sigma

S-(5′-Adenosyl)-L-homocysteine

crystalline

Synonym: 5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine

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Properties

Related Categories Amino Acid, Amino Acid Library Collection, Bioactive Small Molecules for Epigenetic Research, Cell Biology, Epigenetics,
InChI Key   ZJUKTBDSGOFHSH-WFMPWKQPSA-N
Quality Level   PREMIUM
form   crystalline
solubility   1 M HCl: soluble19.60 - 20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow
storage temp.   −20°C

Description

Packaging

10 mg in autosample vial

25, 50, 100 mg in glass bottle

Application

SAH is suitable for use:
• to investigate whether AdoHcy competes with AdoMet in the down-regulation of reporter activity of LUC reporter gene
• as a reagent to study the abundance patterns of SAH and its correlation with vertebrate metamorphosis
• in the optimization of the protein (lysine K) methyltransferase SET7/9 activity assay
• in the fluorescence polarization (FP) assay during dengue virus methyltransferase activity measurement
• as a standard for the measurement of SAH from blood samples by high performance liquid chromatography (HPLC) with fluorimetric detection method

Biochem/physiol Actions

S-(5′-Adenosyl)-L-homocysteine (AdoHcy/SAH) is a component of intracellular homocysteine stress. AdoHcy is a competitive inhibitor (versus AdoMet) of DNA methyltransferases (S-adenosyl-L-methionine (AdoMet)-dependent methyltransferases) involved in epigenetics. Consequently, AdoHcy is used in a variety of studies on epigenetics in hyperhomocysteinemic states. AdoHcy is metabolized by S-adenosylhomocysteine hydrolase (AHCY). AdoHcy is the product of enzymatic transmethylation reactions involving S-Adenosylmethionine (SAM). It is reconverted to SAM by its cleavage into adenosine and L-homocysteine, a substrate of thetin-homocysteine S-methyltransferase. The concentration alterations of SAM and SAH in plasma serve as predictors of cellular methylation potential and metabolic alterations. Methylation capacity indicates specific genetic polymorphisms and/or nutritional deficiencies. Methylation is important in epigenetics, reprogramming, and cancer.

Price and Availability


All labs need water
Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Histone Modification and Chromatin Remodeling

Gene expression is governed by complex mechanisms including transcription factor binding to DNA and coordinated changes in chromatin structure. The primary protein components of chromatin are the his...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 10–16
Keywords: Acetylations, Amplification, Cancer, Cell culture, Chromatin immunoprecipitation, Cloning, DNA purification, Diseases, Gene expression, Immunoprecipitation, Indicators, Methylations, Microarray Analysis, PAGE, Polymerase chain reaction, Polymerase chain reaction - quantitative, Polymorphisms, Purification, Sequencing, Transcription, Whole genome amplification

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

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