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| | 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE Basic information |
| | 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE Chemical Properties |
| Melting point | 209-211 °C | | Boiling point | 787.5±70.0 °C(Predicted) | | density | 1.91±0.1 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | 1 M HCl: soluble19.60 - 20.40mg/mL, clear to slightly hazy, colorless to faintly yellow | | form | crystalline | | pka | 2.22±0.10(Predicted) | | color | Off-White to Brown | | BRN | 99188 | | Stability: | Hygroscopic | | Major Application | pharmaceutical (small molecule) | | InChIKey | ZJUKTBDSGOFHSH-WFMPWKQPSA-N | | SMILES | C(O)(=O)[C@H](CCSC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](O)[C@@H]1O)N | | CAS Number Unlabeled | 979-92-0 |
| WGK Germany | 3 | | F | 8-10-23 | | HS Code | 2934990002 | | Storage Class | 11 - Combustible Solids |
| | 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE Usage And Synthesis |
| Description | S-Adenosyl-L-homocysteine (SAH) is an amino acid derivative and an intermediate, by-product, or modulator of several metabolic pathways, including the activated methyl cycle and cysteine biosynthesis. It is also a product of S-adenosyl-methionine (SAM)-dependent methylation of biological molecules, including DNA, RNA, and histones and other proteins. SAH is a risk factor for many diseases, including cancer and neurodegenerative diseases. In addition, inhibitors that block its hydrolysis are being developed as anti-viral, anti-parasitic, anti-arthritic and immunosuppressive agents. | | Chemical Properties | Pale Beige Solid | | Uses | A novel biomarker for predicting susceptibility of a subject to a mental or neurodegenerative disorder. | | Uses | 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
| | Definition | ChEBI: The S-adenosyl derivative of L-homocysteine. | | 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. | | Purification Methods | It has been recrystallised several times from aqueous EtOH or H2O to give small prisms and has max 260nm in H2O. The picrate has m 170o(dec) from H2O. [Baddiley & Jameison J Chem Soc 1085 1955, de la Haba & Cantoni J Biol Chem 234 603 1959, Borchardt et al. J Org Chem 41 565 1976, NMR: Follmann et al. Eur J Biochem 47 187 1974, Beilstein 26 III/IV 3676.] | | References | [1] NATHAN P COUSSENS. High-throughput screening with nucleosome substrate identifies small-molecule inhibitors of the human histone lysine methyltransferase NSD2.[J]. The Journal of Biological Chemistry, 2018: 13750-13765. DOI: 10.1074/jbc.ra118.004274 |
| | 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE Preparation Products And Raw materials |
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