Synthesis of Two Novel Cysteine-Functionalized Thiophenes

Rita Cagnoli; Massimiliano Lanzi; Adele Mucci; Francesca Parenti; Luisa Schenetti

doi:10.1055/s-2004-834930

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Synthesis of Two Novel Cysteine-Functionalized Thiophenes

Rita Cagnoli^a, Massimiliano Lanzi^b, Adele Mucci*^a, Francesca Parenti^a, Luisa Schenetti^a
^a Dipartimento di Chimica, Università di Modena e Reggio Emilia, via G. Campi 183, 41100 Modena, Italy
Fax: +39(059)373543; e-Mail: mucci.adele@unimore.it;
^b Dipartimento di Chimica Industriale e dei Materiali, Università di Bologna, viale Risorgimento 4, 40136 Bologna, Italy

Abstract

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Abstract

The synthetic approach to methyl N-(tert-butoxycarbonyl)-S-(3-thienyl)-l-cysteinate (1) and methyl N-(tert-butoxycarbonyl)-S-[2-(3-thienyl)ethyl]-l-cysteinate (2) through tosylate inter-mediates is reported and discussed. These compounds, which combine the properties of the cysteine side-chain with those of the thiophene ring represent both potential bioactive molecules and interesting synthons for the development of new materials.

Key words

cysteine - thiophenes - sulfur heterocycles - serine - nucleophilic substitution

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