S-Adenosyl-DL-methionine

Base Information

• Chemical Name: S-Adenosyl-DL-methionine
• CAS No.: 17176-17-9
• Molecular Formula: C₁₅H₂₂N₆O₅S
• Molecular Weight: 398.443
• DSSTox Substance ID: DTXSID40169160
• ChEMBL ID: CHEMBL24991
• Mol file: 17176-17-9.mol

Synonyms:S-Adenosyl-DL-methionine;17176-17-9;2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate;Ademetionine [USAN:INN];Methionine, S-adenosyl-, DL-;Transmetil (TN);SCHEMBL25176;CHEMBL24991;DTXSID40169160;MS-26736;HY-126126;CS-0090603;D07128;F82382;Adenosine, 5'-((3-amino-3-carboxypropyl)methylsulfonio)-5'-deoxy-, inner salt;(+-)-5'-((R*)-((R*)-3-Amino-3-carboxypropyl)methylsulfonio)-5'-deoxyadenosine hydroxide, inner salt

Chemical Property of S-Adenosyl-DL-methionine

Chemical Property:

• Melting Point: 78℃
• PSA: 273.51000
• LogP: 1.33920
• Storage Temp.: −20°C
• Solubility.: H2O: soluble100mg/mL
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 398.13723900
• Heavy Atom Count: 27
• Complexity: 527

Purity/Quality:

99%, ^*data from raw suppliers

S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt from yeast ( ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[S+](CCC(C(=O)[O-])N)CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: C[S+](CCC(C(=O)[O-])N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O

Technology Process of S-Adenosyl-DL-methionine

There total 10 articles about S-Adenosyl-DL-methionine 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:

L-methionine (63-68-3,26062-47-5,58576-49-1) + ATP (56-65-5,896506-78-8) → 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'-Deoxy-5'-methylthioadenosine (2457-80-9)

Guidance literature:

With recombinant Methanocaldococcus jannaschii methionine adenosyltransferase; potassium chloride; magnesium chloride; In aq. buffer; at 65 ℃; for 4h; pH=8; Temperature; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/anie.201308272

Reference yield:

1-methylhexahydropyrylium tetrafluoroborate (6914-65-4) + S-(5'-adenosyl)-L-homocysteine (979-92-0) → 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)

Guidance literature:

1-methylhexahydropyrylium tetrafluoroborate; S-(5'-adenosyl)-L-homocysteine; With sulfuric acid; trifluoroacetic acid; at 0 ℃;

In dichloromethane; water; Product distribution / selectivity;

Reference yield:

1-methyloxiranium tetrafluoroborate (20725-78-4) + S-(5'-adenosyl)-L-homocysteine (979-92-0) → 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)

Guidance literature:

1-methyloxiranium tetrafluoroborate; S-(5'-adenosyl)-L-homocysteine; With sulfuric acid; trifluoroacetic acid; at 0 ℃;

In dichloromethane; water; Product distribution / selectivity;

upstream raw materials:

methyl iodide

S-(5'-adenosyl)-L-homocysteine

D-Glucose

L-methionine

Downstream raw materials:

N-Methylnicotinium

R-(+)-N'-methylnicotinium ion

R-(+)-N-methylnicotinium ion

retusin

Refernces

• 1、 Zhang, Zhengan,Mahanta, Nilkamal,Hudson, Graham A.,Mitchell, Douglas A.,Van Der Donk, Wilfred A.. "Mechanism of a Class C Radical S-Adenosyl- l -methionine Thiazole Methyl Transferase". . p. 18623 - 18631. Retrieved 2017/12/26.
• 2、 -. "Chemical Synthesis Of S-Adenosyl-L-Methionine With Enrichment Of (S,S)-Isomer". Page/Page column 4; 5. . Retrieved 2008/06/13.