Merck
All Photos(4)

A9384

Sigma-Aldrich

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:
Molecular Weight:
384.41
Beilstein:
99188
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.51

Quality Level

form

crystalline

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

Packaging

10, 25, 50, 100 mg in glass bottle

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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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Product Information Sheet

More documents

Quotes and Ordering

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
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)
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

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