All Photos(4)
Synonym(s):
5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine
Empirical Formula (Hill Notation):
C14H20N6O5S
CAS Number:
Molecular Weight:
384.41
Beilstein:
99188
EC Number:
MDL number:
UNSPSC Code:
41106305
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.51
Recommended Products
Assay
≥98.0% (HPLC)
≥98.0% (TLC)
Quality Level
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
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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
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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Desirée E C Smith et al.
Clinical chemistry and laboratory medicine, 50(9), 1641-1647 (2012-09-11)
Disturbances in the levels of one-carbon (1C) metabolism metabolites have been associated with a wide variety of neuropsychiatric diseases. Cerebrospinal fluid (CSF) levels of homocysteine (Hcy) and the other 1C metabolites, nor their interrelatedness and putative determinants, have been studied
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
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
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