A9384

S-(5′-Adenosyl)-L-homocysteine

crystalline

• Synonym(s): 5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine
• Empirical Formula (Hill Notation): C₁₄H₂₀N₆O₅S
• CAS Number: 979-92-0
• Molecular Weight: 384.41
• Beilstein/REAXYS Number: 99188
• EC Number: 213-560-8
• MDL number: MFCD00037388
• UNSPSC Code: 41106305
• eCl@ss: 32160406
• PubChem Substance ID: 24891441
• NACRES: NA.51

Properties

• assay: ≥98.0% (HPLC); ≥98.0% (TLC)
• Quality Level: 300
• form: crystalline
• mol wt: 384.41
• solubility: 1 M HCl: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow
• storage temp.: −20°C
• SMILES string: 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
• InChI key: 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[1]
• as a reagent to study the abundance patterns of SAH and its correlation with vertebrate metamorphosis[2]
• in the optimization of the protein (lysine K) methyltransferase SET7/9 activity assay[3]
• in the fluorescence polarization (FP) assay during dengue virus methyltransferase activity measurement[4]
• as a standard for the measurement of SAH from blood samples by high performance liquid chromatography (HPLC) with fluorimetric detection method[5]

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.[6] 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.[7] Methylation is important in epigenetics, reprogramming, and cancer.[2]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)