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Molecules 2014, 19(1), 1023-1033; doi:10.3390/molecules19011023
Article

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

1,* , 2
 and 3
Received: 14 November 2013; in revised form: 19 December 2013 / Accepted: 20 December 2013 / Published: 15 January 2014
(This article belongs to the Section Organic Synthesis)
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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 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.
Keywords: 1-benzyl-2-(methylthio)-5-imidazole carbonitrile; ethyl-1-benzyl-5-imidazol-carboxylate; N-diphenylmethylene glycine tert-butyl ester; O’Donnell method 1-benzyl-2-(methylthio)-5-imidazole carbonitrile; ethyl-1-benzyl-5-imidazol-carboxylate; N-diphenylmethylene glycine tert-butyl ester; O’Donnell method
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Talab, S.; Taha, K.K.; Lugtenburg, J. Preparation of 2'-13C-L-Histidine Starting from 13C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine. Molecules 2014, 19, 1023-1033.

AMA Style

Talab S, Taha KK, Lugtenburg J. Preparation of 2'-13C-L-Histidine Starting from 13C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine. Molecules. 2014; 19(1):1023-1033.

Chicago/Turabian Style

Talab, Sarra; Taha, Kamal K.; Lugtenburg, Johan. 2014. "Preparation of 2'-13C-L-Histidine Starting from 13C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine." Molecules 19, no. 1: 1023-1033.


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