Preparation of 2 '-C-13-L-Histidine starting from C-13-Thiocyanate
| Autor: | Sarra Talab, Kamal K. Taha, Johan Lugtenburg |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
ethyl-1-benzyl-5-imidazol-carboxylate
Pharmaceutical Science Glycin Chloride Article N-diphenylmethylene glycine tert-butyl ester Analytical Chemistry Isotopomers lcsh:QD241-441 chemistry.chemical_compound 1-benzyl-2-(methylthio)-5-imidazole carbonitrile lcsh:Organic chemistry Drug Discovery medicine Organic chemistry Imidazole Histidine Carbon Radioisotopes Physical and Theoretical Chemistry O’Donnell method Enantiomeric excess Thiocyanate Chemistry Organic Chemistry Imidazoles Combinatorial chemistry Cyclization Chemistry (miscellaneous) Isotope Labeling Yield (chemistry) Molecular Medicine Thiocyanates medicine.drug |
| Zdroj: | Molecules Molecules, Vol 19, Iss 1, Pp 1023-1033 (2014) Molecules, 19(1), 1023-1033 Volume 19 Issue 1 Pages 1023-1033 |
| Popis: | 1-Benzyl-2-(methylthio)-imidazole-5-ketone is obtained in a few simple steps starting from thiocyanate and glycine amide (glycin). Subsequent treatment with diethyl phosphorocyanidate and functional group manipulations gives 1-benzyl-5-chloromethyl-imidazolium chloride. This compound is converted under mild O’Donnell conditions into the corresponding L-histidine derivative. After deprotection L-histidine is obtained in good yield and 99% enantiomeric excess. 2'-13C-L-Histidine has been obtained via this new scheme with high (99%) 13C incorporation starting with commercially available 13C- thiocyanate. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives. |
| Databáze: | OpenAIRE |
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