| Autor: |
R. J. H. Luiten, K. D. Witters, Jan Raap, Johan Lugtenburg, J. Baart, P. J. E. Verdegem, A. C. Hoek, J. J. Cappon |
| Rok vydání: |
2010 |
| Předmět: |
|
| Zdroj: |
Recueil des Travaux Chimiques des Pays-Bas. 113:318-328 |
| ISSN: |
0165-0513 |
| DOI: |
10.1002/recl.19941130603 |
| Popis: |
(2′-13C)-, (1′-15N)- and (3′-15N)-L-Histidine were prepared according to a synthetic scheme that allows the 13C or 15N labelling of all carbon and nitrogen positions or any combination of positions. A 1,5-disubstituted imidazole ring was constructed via condensation of tosylmethyl isocyanide with 3-phenylpropenal and subsequent cycloaddition of benzylamine. The imidazole intermediate was converted into 1-benzyl-5-(chloromethyl)-imidazolium chloride which was coupled to a glycine moiety via an enantioselective coupling with the bislactim ether of cyclo-D-valylglycine. Deprotection of the coupling product afforded L-histidine in high optical purity. Syntheses for the isotopically labelled synthons were developed starting from simple, commercially available, highly enriched compounds. The labelled L-histidines were characterized by mass spectrometry and 1H-, 13C- and 15N-NMR spectroscopy. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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