Synthesis 2011(2): 235-242  
DOI: 10.1055/s-0030-1258354
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Toward the Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs

Vanessa Legrosa, Florian Hamona, Bruno Violeaua, Frédéric Turpinb, Florence Djedaini-Pilardc, Jérôme Désiréa, Christophe Len*d
a Université de Poitiers, UMR 6514 CNRS, Synthèse et Réactivité des Substances Naturelles, 40 avenue du Recteur Pineau, 86022 Poitiers cedex, France
b Biocydex, 40 avenue du Recteur Pineau, 86022 Poitiers cedex, France
c Université de Picardie Jules Verne, UMR 6219 CNRS, Laboratoire des Glucides, 33 rue Saint Leu, 80039 Amiens, France
d Université de Technologie de Compiègne, Ecole Supérieure de Chimie Organique et Minérale, EA 4297 UTC/ESCOM, 1 allée du Réseau Jean-Marie Buckmaster, 60200 Compiègne, France
Fax: +33(3)44971591; e-Mail: christophe.len@utc.fr;
Further Information

Publication History

Received 1 September 2010
Publication Date:
10 December 2010 (online)

Abstract

The synthesis of eleven new cyclodextrin derivatives having nucleobase moiety - thymin-1-yl, adenin-9-yl, and guanin-9-yl - is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl group. Direct nucleophilic substitution and 1,3-dipolar cycloaddition were performed in good yields (13-73%) for some of the synthesized compounds.

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6-Azido-β-CD, 6-amino-β-CD, 6-azido permethylated and 6-amino permethylated β-CD derivatives were furnished by Biocydex.