Lugtenburg, J.

Taha, K.K.

Talab, S.

Molecules

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

Sarra Talab

Kamal Khalifa Taha

Johan Lugtenburg

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Preparation of 2'-13C-L-Histidine Starting from  13C-Thiocyanate: Synthetic Access to Any Site-Directed  Stable Isotope Enriched L-Histidine

Leiden University Scholary Publications

Preparation of 2 '-C-13-L-Histidine starting from C-13-Thiocyanate: synthetic access to any site-directed stable isotope enriched L-Histidine

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Preparation of 2 '-C-13-L-Histidine starting from C-13-Thiocyanate: synthetic access to any site-directed stable isotope enriched L-Histidine

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Leiden University Scholary Publications