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Synthesis 2011(11): 1759-1770  
DOI: 10.1055/s-0030-1260033
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Biological Evaluation of Modified 2-Deoxystreptamine Dimers

Gérald Costea, Tim Horlacherb, Lidia Molinac, Antonio J. Moreno-Vargas*c, Ana T. Carmonac, Inmaculada Robinac, Peter H. Seebergerb,d, Sandrine Gerber-Lemaire*a
a Laboratory of Glycochemistry and Asymmetric Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, Batochime, 1015 Lausanne, Switzerland
Fax: +41(21)6939355; e-Mail: Sandrine.Gerber@epfl.ch;
b Department for Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
c Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Profesor García González 1, 41012 Sevilla, Spain
Fax: +34(954)624960; e-Mail: ajmoreno@us.es;
d Institute for Chemistry and Biochemistry, Frei Universität Berlin, Arnimallee 22, 14195 Berlin, Germany
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Publication History

Received 3 November 2010
Publication Date:
06 May 2011 (online)

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Abstract

Aminoglycosides are powerful antibiotics, but the emergence of resistant bacterial strains has prompted the search for analogues with better pharmacological profiles. The synthesis of 2-deoxystreptamine (2-DOS) dimers linked by polyamines and analogues based on furylcarbopeptoid skeletons is described. Potent and selective ligands for bacterial 16S rRNA were identified using microarray techniques by determining the affinity of these derivatives toward bacterial and human ribosomal RNAs.

Key words

antibiotics - 2-deoxystreptamine dimers - microarray - ribosomal RNA - solid-phase synthesis