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

S Talab, KK Taha, J Lugtenburg

Index: Talab, Sarra; Taha, Kamal Khalifa; Lugtenburg, Johan Molecules, 2014 , vol. 19, # 1 p. 1023 - 1033

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Abstract

Abstract 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 ...