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About This Item
Empirical Formula (Hill Notation):
C14H20N6O5S
CAS Number:
Molecular Weight:
384.41
NACRES:
NA.51
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
41106305
EC Number:
213-560-8
MDL number:
Beilstein/REAXYS Number:
99188
Quality Level
assay
≥98.0% (HPLC), ≥98.0% (TLC)
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
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Related Content
Product Information Sheet
Siew Pheng Lim et al.
Methods in molecular biology (Clifton, N.J.), 1030, 249-268 (2013-07-04)
Flavivirus NS5 is the most conserved protein amongst the flavivirus proteins and is an essential enzyme for viral mRNA capping and replication. It encodes a methyl-transferase (MTase) domain at its N-terminal region which carries out sequential N7 and 2'-O methylation
E A Struys et al.
Clinical chemistry, 46(10), 1650-1656 (2000-10-06)
Available methods for the determination of nanomolar concentrations of S:-adenosylmethionine (SAM) and S:-adenosylhomocysteine (SAH) in plasma and cerebrospinal fluid (CSF) are time-consuming. We wished to develop a method for their rapid and simultaneous measurement. We used tandem mass spectrometry (MS/MS)
S Melnyk et al.
Clinical chemistry, 46(2), 265-272 (2000-02-05)
The relative changes in plasma and intracellular concentrations of S-adenosylmethionine (SAM) and S-adenosylhomocysteine (SAH) may be important predictors of cellular methylation potential and metabolic alterations associated with specific genetic polymorphisms and/or nutritional deficiencies. Because these metabolites are present in nanomolar