S-adenosyl-L-homocysteine

Base Information

• Chemical Name: S-adenosyl-L-homocysteine
• CAS No.: 979-92-0
• Molecular Formula: C14H20N6O5S
• Molecular Weight: 384.416
• Hs Code.: 2934990002
• European Community (EC) Number: 213-560-8
• UNII: 8K31Q2S66S
• DSSTox Substance ID: DTXSID30895860
• Nikkaji Number: J14.397I
• Wikipedia: S-Adenosyl-L-homocysteine
• Wikidata: Q307434
• NCI Thesaurus Code: C103149
• Pharos Ligand ID: J9G4V25XXVU4
• Metabolomics Workbench ID: 37510
• ChEMBL ID: CHEMBL418052
• Mol file: 979-92-0.mol

Synonyms:Adenosylhomocysteine, S;S Adenosylhomocysteine;S-Adenosylhomocysteine

Chemical Property of S-adenosyl-L-homocysteine

Chemical Property:

• Appearance/Colour: Colorless cluster crystals
• Melting Point: 209-211 °C
• Boiling Point: 787.457 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 430.038 °C
• PSA: 207.93000
• Density: 1.912 g/cm³
• LogP: -0.15560
• Storage Temp.: −20°C
• Solubility.: 1 M HCl: soluble19.60 - 20.40mg/mL, clear to slightly hazy, colo
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 384.12158893
• Heavy Atom Count: 26
• Complexity: 504

Purity/Quality:

98%,99%, ^*data from raw suppliers

S-adenosylhomocysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CSCCC(C(=O)O)N)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CSCC[C@@H](C(=O)O)N)O)O)N
• 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.
• Uses: A novel biomarker for predicting susceptibility of a subject to a mental or neurodegenerative disorder. SAH is suitable for use:to investigate whether AdoHcy competes with AdoMet in the down-regulation of reporter activity of LUC reporter geneas a reagent to study the abundance patterns of SAH and its correlation with vertebrate metamorphosisin the optimization of the protein (lysine K) methyltransferase SET7/9 activity assayin the fluorescence polarization (FP) assay during dengue virus methyltransferase activity measurementas a standard for the measurement of SAH from blood samples by high performance liquid chromatography (HPLC) with fluorimetric detection method

Technology Process of S-adenosyl-L-homocysteine

There total 46 articles about S-adenosyl-L-homocysteine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.5%

AdoHcy (40950-52-5) → S-(5'-adenosyl)-L-homocysteine (979-92-0)

Guidance literature:

With sulfuric acid; at 40 ℃; overnight;

Reference yield: 81.0%

(S)-4-[(2S,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-2-(2,2,2-trifluoro-acetylamino)-butyric acid methyl ester (100804-01-1) → S-(5'-adenosyl)-L-homocysteine (979-92-0)

Guidance literature:

With barium dihydroxide; In methanol; water; for 2h; Ambient temperature;

DOI:10.1055/s-1985-31385

Reference yield:

S-Adenosyl-L-methionine (14031-35-7,17176-17-9,29908-03-0,75044-81-4,78548-84-2,79647-17-9,91279-78-6) → 5'-deoxyadenosine (4754-39-6) + S-(5'-adenosyl)-L-homocysteine (979-92-0)

Guidance literature:

With sodium sulfide; nitrogenase cofactor synthase NifB from Methanotrix thermoacetophila; dithionite^(2-); iron(II) sulfate; In aq. buffer; at 30 ℃; for 1h; pH=7.4; Reagent/catalyst; Catalytic behavior; Enzymatic reaction;

DOI:10.1021/jacs.0c02243

upstream raw materials:

AdoHcy

2-amino-4-mercaptobutyric acid

ATP

adenosine

Downstream raw materials:

S-Adenosyl-L-methionine

S-adenosyl-L-methionine

Refernces

• 1、 Lin, Zhenjian,Torres, Joshua P.,Ammon, Mary Anne,Marett, Lenny,Teichert, Russell W.,Reilly, Christopher A.,Kwan, Jason C.,Hughen, Ronald W.,Flores, Malem,Tianero, Ma. Diarey,Peraud, Olivier,Cox, James E.,Light, Alan R.,Villaraza, Aaron Joseph L.,Haygood, Margo G.,Concepcion, Gisela P.,Olivera, Baldomero M.,Schmidt, Eric W.. "A bacterial source for mollusk pyrone polyketides". . p. 73 - 81. Retrieved 2013.
• 2、 Wang,Y.,Hogenkamp,H.P.. "-". . p. 998. Retrieved 1978.
• 3、 Rust, Heather L.,Zurita-Lopez, Cecilia I.,Clarke, Steven,Thompson, Paul R.. "Mechanistic studies on transcriptional coactivator protein arginine methyltransferase 1". . p. 3332 - 3345. Retrieved 2011.
• 4、 Hemeon, Ivan,Gutierrez, Jemy A.,Ho, Meng-Chiao,Schramm, Vern L.. "Characterizing DNA methyltransferases with an ultrasensitive luciferase-linked continuous assay". . p. 4996 - 5004. Retrieved 2011.
• 5、 Echavarri-Erasun, Carlos,Fajardo, Ana Sosa,Legrand, Pierre,Martin, Lydie,Nicolet, Yvain,Payá-Tormo, Luc?a,Pellicer Mart?nez, Maria Teresa,Rubio, Luis M.,Vernède, Xavier. "Structural Insights into the Mechanism of the Radical SAM Carbide Synthase NifB, a Key Nitrogenase Cofactor Maturating Enzyme". supporting information. p. 11006 - 11012. Retrieved 2020/07/13.
• 6、 Zhang, Chi,Chen, Xinlu,Crandall-Stotler, Barbara,Qian, Ping,K?llner, Tobias G.,Guo, Hong,Chen, Feng. "Biosynthesis of methyl (E)-cinnamate in the liverwort Conocephalum salebrosum and evolution of cinnamic acid methyltransferase". . p. 50 - 59. Retrieved 2019/05/14.