A9384

S-(5′-Adenosyl)-L-homocysteine

crystalline

• Sinónimos: 5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine
• Fórmula empírica (notación de Hill): C₁₄H₂₀N₆O₅S
• Número de CAS: 979-92-0
• Peso molecular: 384.41
• Beilstein: 99188
• Número CE: 213-560-8
• Número MDL: MFCD00037388
• Código UNSPSC: 41106305
• eCl@ss: 32160406
• ID de la sustancia en PubChem: 24891441
• NACRES: NA.51

Propiedades

• Ensayo: ≥98.0% (HPLC); ≥98.0% (TLC)
• Nivel de calidad: 300
• Formulario: crystalline
• mol peso: 384.41
• solubilidad: 1 M HCl: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow
• temp. de almacenamiento: −20°C
• cadena 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
• Clave InChI: ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Descripción

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)