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A9384

Sigma-Aldrich

S-(5′-Adenosyl)-L-homocysteine

crystalline

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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/REAXYS Number:
99188
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.51

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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1 of 4

This Item
C913743713A2846
S-(5′-Adenosyl)-L-homocysteine crystalline

A9384

S-(5′-Adenosyl)-L-homocysteine

S-(5′-Adenosyl)-3-thiopropylamine ≥98.0% (HPLC)

43713

S-(5′-Adenosyl)-3-thiopropylamine

A-134974 dihydrochloride hydrate ≥98% (HPLC), solid

A2846

A-134974 dihydrochloride hydrate

assay

≥98.0% (HPLC), ≥98.0% (TLC)

assay

≥95%

assay

≥98.0% (HPLC)

assay

≥98% (HPLC)

Quality Level

300

Quality Level

-

Quality Level

-

Quality Level

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

mol wt

384.41

mol wt

491.18  g/mol

mol wt

-

mol wt

-

solubility

1 M HCl: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

-

solubility

-

solubility

H2O: soluble

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.

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)


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Yukako Chiba et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(18), 10225-10230 (2003-08-23)
Cystathionine gamma-synthase, the first committed enzyme of methionine biosynthesis in higher plants, is encoded by the CGS1 gene in Arabidopsis thaliana. We have shown previously that the stability of the CGS1 mRNA is negatively regulated in response to methionine application
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
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 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)

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