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Synthesis 2010(18): 3131-3137  
DOI: 10.1055/s-0030-1258188
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Straightforward Method for the Synthesis of Selenocysteine and Selenocystine Derivatives from l-Serine Methyl Ester

Antonio L. Braga*a, Ludger A. Wessjohannb, Paulo S. Taubea, Fábio Z. Galettoa,c, Fabiano M. de Andradec
a Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, 88040-970, Brazil
b Leibniz Institute of Plant Biochemistry, Bioorganic Chemistry, Weinberg 3, 06120 Halle, Germany
c Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97105-900, Brazil
Fax: +55(48)37216850; e-Mail: albraga@qmc.ufsc.br;
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Publikationsverlauf

Received 8 March 2010
Publikationsdatum:
22. Juli 2010 (online)

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Abstract

A set of selenoamino acids has been efficiently synthesized under smooth conditions by a simple, flexible and modular strategy. In this method, O-mesylated l-serine methyl ester is generated in situ and directly substituted with various selenolate anions to afford selenocysteine, selenolanthionine, and selenocystine derivatives in good yields. Also, a tellurocysteine derivative can be obtained by this method.

Key words

organoselenium - selenoamino acids - selenocysteine - selenocystine - tellurocysteine

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