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

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 un...

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Detalles Bibliográficos
Autores principales: Talab, Sarra, Taha, Kamal Khalifa, Lugtenburg, Johan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271553/
https://www.ncbi.nlm.nih.gov/pubmed/24434674
http://dx.doi.org/10.3390/molecules19011023
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author Talab, Sarra
Taha, Kamal Khalifa
Lugtenburg, Johan
author_facet Talab, Sarra
Taha, Kamal Khalifa
Lugtenburg, Johan
author_sort Talab, Sarra
collection PubMed
description 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'-(13)C-L-Histidine has been obtained via this new scheme with high (99%) (13)C incorporation starting with commercially available (13)C- thiocyanate. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives.
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spelling pubmed-62715532018-12-20 Preparation of 2'-(13)C-L-Histidine Starting from (13)C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine Talab, Sarra Taha, Kamal Khalifa Lugtenburg, Johan Molecules Article 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'-(13)C-L-Histidine has been obtained via this new scheme with high (99%) (13)C incorporation starting with commercially available (13)C- thiocyanate. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives. MDPI 2014-01-15 /pmc/articles/PMC6271553/ /pubmed/24434674 http://dx.doi.org/10.3390/molecules19011023 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Talab, Sarra
Taha, Kamal Khalifa
Lugtenburg, Johan
Preparation of 2'-(13)C-L-Histidine Starting from (13)C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine
title Preparation of 2'-(13)C-L-Histidine Starting from (13)C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine
title_full Preparation of 2'-(13)C-L-Histidine Starting from (13)C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine
title_fullStr Preparation of 2'-(13)C-L-Histidine Starting from (13)C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine
title_full_unstemmed Preparation of 2'-(13)C-L-Histidine Starting from (13)C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine
title_short Preparation of 2'-(13)C-L-Histidine Starting from (13)C-Thiocyanate: Synthetic Access to Any Site-Directed Stable Isotope Enriched L-Histidine
title_sort preparation of 2'-(13)c-l-histidine starting from (13)c-thiocyanate: synthetic access to any site-directed stable isotope enriched l-histidine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271553/
https://www.ncbi.nlm.nih.gov/pubmed/24434674
http://dx.doi.org/10.3390/molecules19011023
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AT lugtenburgjohan preparationof213clhistidinestartingfrom13cthiocyanatesyntheticaccesstoanysitedirectedstableisotopeenrichedlhistidine

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