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A9384

Sigma-Aldrich

S-(5′-Adenosyl)-L-homocysteine

crystalline

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C14H20N6O5S
Numéro CAS:
979-92-0
Poids moléculaire :
384.41
Numéro Beilstein :
99188
Numéro CE :
213-560-8
Numéro MDL:
MFCD00037388
Code UNSPSC :
41106305
eCl@ss :
32160406
ID de substance PubChem :
24891441
Nomenclature NACRES :
NA.51

Pureté

≥98.0% (HPLC)
≥98.0% (TLC)

Niveau de qualité

300

Forme

crystalline

Poids mol.

384.41

Solubilité

1 M HCl: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow

Température de stockage

−20°C

Chaîne SMILES 

N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(O)=O

InChI

1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1

Clé InChI

ZJUKTBDSGOFHSH-WFMPWKQPSA-N

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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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

Yukako Chiba et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(18), 10225-10230 (2003-08-23)
Cystathionine gamma-synthase, the first committed enzyme of methionine biosynthesis in higher plants, is encoded by the CGS1 gene in Arabidopsis thaliana. We have shown previously that the stability of the CGS1 mRNA is negatively regulated in response to methionine application
J Wang et al.
Thrombosis and haemostasis, 70(6), 1047-1052 (1993-12-20)
Elevated plasma homocysteine is associated with an increased risk of intravascular thrombosis. Platelet aggregation and thrombosis are inhibited by prostacyclin produced by the vascular endothelium. Our aim was to investigate whether homocysteine and related metabolites inhibit endothelial prostacyclin production. We
S C Lu
The international journal of biochemistry & cell biology, 32(4), 391-395 (2000-04-13)
S-Adenosyl-Lmethionine (SAM) is an important molecule in normal cell function and survival. SAM is utilized by three key metabolic pathways: transmethylation; transsulfuration; and polyamine synthesis. In transmethylation reactions, the methyl group of SAM is donated to a large variety of
Determination of S-adenosylmethionine and S-adenosylhomocysteine from human blood samples by HPLC-FL
Birsan, Camelia, et al.
Analytical Letters, 41, 1720-1731 (2008)
Wenyu Yu et al.
Bioorganic & medicinal chemistry, 21(7), 1787-1794 (2013-02-26)
Chemical inhibition of proteins involved in chromatin-mediated signaling is an emerging strategy to control chromatin compaction with the aim to reprogram expression networks to alter disease states. Protein methyltransferases constitute one of the protein families that participate in epigenetic control
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Histone Modification and Chromatin Remodeling | Epigenetics

Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.

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