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

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

1
Department of Chemistry, College of Applied and Industrial Science, University of Bahri, P.O. Box 11111, Khartoum 1660, Sudan
2
Department of Chemistry, College of Science, AI Imam Mohammad Ibn Saud Islamic University(IMSIU), P.O. Box 5701, Riyadh 11432, Kingdom of Saudi Arabia
3
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands
*
Author to whom correspondence should be addressed.
Received: 14 November 2013 / Revised: 19 December 2013 / Accepted: 20 December 2013 / Published: 15 January 2014
(This article belongs to the Section Organic Chemistry)
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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. View Full-Text
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
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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.

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