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Merck

A9384

S-(5′-Adenosyl)-L-homocysteine

crystalline

Sinónimos:

5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine

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Fórmula empírica (notación de Hill):
C14H20N6O5S
Número CAS:
979-92-0
Peso molecular:
384.41
NACRES:
NA.51
PubChem Substance ID:
24891441
eCl@ss:
32160406
UNSPSC Code:
41106305
EC Number:
213-560-8
MDL number:
MFCD00037388
Beilstein/REAXYS Number:
99188

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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

SMILES string

N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(O)=O

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

Quality Level

300

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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.

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000510739
0000510739
0000483755
0000483755
0000483754

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S C Lu
The international journal of biochemistry & cell biology, 32(4), 391-395 (2000-04-13)
S-Adenosyl-Lmethionine (SAM) is an important molecule in normal cell function and survival. SAM is utilized by three key metabolic pathways: transmethylation; transsulfuration; and polyamine synthesis. In transmethylation reactions, the methyl group of SAM is donated to a large variety of
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
J Metz
Annual review of nutrition, 12, 59-79 (1992-01-01)
Neuropathy commonly complicates cobalamin (Cb1) deficiency in humans, monkeys, fruit bats, and pigs. The neuropathy is characterized by demyelination of the posterolateral columns of the spinal cord (subacute combined degeneration). The lesion was thought to arise primarily from impairment of
Determination of S-adenosylmethionine and S-adenosylhomocysteine from human blood samples by HPLC-FL
Birsan, Camelia, et al.
Analytical Letters, 41, 1720-1731 (2008)
Wenyu Yu et al.
Bioorganic & medicinal chemistry, 21(7), 1787-1794 (2013-02-26)
Chemical inhibition of proteins involved in chromatin-mediated signaling is an emerging strategy to control chromatin compaction with the aim to reprogram expression networks to alter disease states. Protein methyltransferases constitute one of the protein families that participate in epigenetic control
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