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% ^*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
• General Description: 5'-Deoxy-S-adenosyl-L-homocysteine (also known as S-adenosylhomocysteine or AdoHcy) is a key metabolic intermediate in methylation reactions, serving as a byproduct of S-adenosylmethionine (SAM)-dependent methyltransferase activity. It is regulated by S-adenosylhomocysteine hydrolase, an enzyme that hydrolyzes AdoHcy into adenosine and homocysteine. The study highlights the enzyme's susceptibility to irreversible inactivation by haloethyl and dihalocyclopropyl esters, which exploit its oxidative rather than hydrolytic function, leading to NAD+ depletion and enzyme inhibition. This mechanism underscores the enzyme's role as a therapeutic target for modulating methylation-dependent pathways in various diseases.

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-(5′-adenosyl)-L-methionine iodide

S-adenosyl-L-homocysteine sulfone

S-adenosyl-L-methionine

Refernces

Inactivation of S-adenosylhomocysteine hydrolase with haloethyl and dihalocyclopropyl esters derived from homoadenosine-6′-carboxylic acid

10.1016/j.bmcl.2004.09.050

The research aimed to develop new inhibitors targeting the hydrolytic activity of S-adenosylhomocysteine (AdoHcy) hydrolase, an enzyme crucial in the regulation of biological methylation reactions, with potential applications in antiviral, antiparasitic, immunosuppressive, and plasma homocysteine-lowering agents. The study focused on a series of haloethyl and dihalocyclopropyl esters derived from homoadenosine-60-carboxylic acid, which were designed to interact with the enzyme. The researchers found that incubation of these esters with the enzyme led to time- and concentration-dependent inactivation of AdoHcy hydrolase and a significant depletion of its NAD+ content. The inactivation was irreversible and was attributed to the enzyme's oxidative activity rather than its hydrolytic activity. The chemicals used in the process included haloethyl esters (2a and 2b) and dihalocyclopropyl esters (3a and 3b), with the dihalocyclopropyl esters showing higher affinity and lower kinact values compared to the haloethyl esters. The study concluded that these esters inactivate AdoHcy hydrolase through a type I mechanism, involving the oxidative activity of the enzyme, rather than acting as substrates for its hydrolytic activity.

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