5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-Adenosine tosylate

Base Information

• Chemical Name: 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-Adenosine tosylate
• CAS No.: 52248-03-0
• Molecular Formula: C22H30N6O8S2
• Molecular Weight: 570.639
• DSSTox Substance ID: DTXSID40436187
• NCI Thesaurus Code: C100098
• Mol file: 52248-03-0.mol

Synonyms:Ademetionine;AdoMet;FO 1561;FO-1561;FO1561;Gumbaral;S Adenosyl L Methionine;S Adenosylmethionine;S Adenosylmethionine Sulfate Tosylate;S Amet;S-Adenosyl-L-Methionine;S-Adenosylmethionine;S-Adenosylmethionine Sulfate Tosylate;SAM-e;Samyr

Chemical Property of 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-Adenosine tosylate

Chemical Property:

• Melting Point: 78℃
• PSA: 273.51000
• LogP: 1.33920
• Storage Temp.: -20°C
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 570.15665428
• Heavy Atom Count: 38
• Complexity: 726

Purity/Quality:

97% ^*data from raw suppliers

5''-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5’-deoxyadenosineTosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)[O-].C[S+](CCC(C(=O)O)N)CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)[O-].C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Recent ClinicalTrials: SAMe Trial for Patients With Alcoholic Cirrhosis
• Recent EU Clinical Trials: SAMe as an epigenetic treatment of depression in people with childhood trauma, a double blind placebo-controlled trial
• Uses: S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt has been used for cell proliferation assay. It has also been used for methylation assay.

Refernces

Characterisation of the broadly-specific O-methyl-transferase jerf from the late stages of jerangolid biosynthesis

10.3390/molecules21111443

The study focuses on the characterization of the O-methyltransferase enzyme JerF, which is involved in the late stages of jerangolid biosynthesis. JerF is unique for its ability to catalyze the formation of a non-aromatic, cyclic methylenolether, a reaction not previously characterized in other O-methyltransferases. The researchers successfully overexpressed JerF in E. coli and utilized cell-free extracts to conduct bioconversion experiments. They also chemically synthesized a range of substrate surrogates to evaluate JerF's catalytic activity and substrate tolerance. The results revealed that JerF has a broad substrate tolerance and high regioselectivity, making it a promising candidate for chemoenzymatic synthesis, particularly for the modification of natural products containing a 4-methoxy-5,6-dihydro-2H-pyran-2-one moiety. The study also highlighted the potential of JerF in introducing specific methylation patterns and its use in biorthogonal coupling reactions, such as click chemistry, for site-specific labeling of biomolecules like DNA, RNA, or proteins.

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