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Synthesis 2012(1): 130-136  
DOI: 10.1055/s-0031-1289609
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of α-Trifluoromethyl-α-hydroxy Acid-Peptide Conjugates via Click Chemistry

Nadezhda V. Sokolovaa, Daria V. Vorobyevab, Sergey N. Osipov*b, Tamara P. Vasilyevab, Valentine G. Nenajdenko*a
a Department of Chemistry, Moscow State University, Leninskie Gory 1, Moscow 119991, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow 119991, Russian Federation
Fax: +7(495)9328846; e-Mail: nen@acylium.chem.msu.ru; e-Mail: osipov@ineos.ac.ru;
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Publication History

Received 9 September 2011
Publication Date:
17 November 2011 (online)

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Abstract

A simple and convenient method for the incorporation of fluorinated α-hydroxy acids into peptides is described. The target conjugates were obtained from α-alkynyl-α-trifluoromethyl-α-hydroxy acids and azido peptides via the copper(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). After straightforward deprotection, the α-trifluoromethyl-α-hydroxy acid containing peptides may find important applications in biochemistry and medicinal chemistry.

Key words

α-trifluoromethyl-α-hydroxy acids - azido peptides - click chemistry - Huisgen cycloaddition reaction - 1,2,3-triazoles

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