A9384

S-(5′-Adenosyl)-L-homocysteine

crystalline

• Synonyme(s) : 5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine
• 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

Propriétés

• 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

Description

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.

Informations sur la sécurité

• 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)