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Synthesis 2011(24): 4059-4067  
DOI: 10.1055/s-0031-1289577
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized Benzoboroxoles for the Construction of Boronolectins

Falk Wienhold, Dorith Claes, Karolina Graczyk, Wolfgang Maison*
Department of Chemistry, University of Hamburg, Bundesstraße 45, 20146 Hamburg, Germany
Fax: +49(40)428386519; e-Mail: maison@chemie.uni-hamburg.de;
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Publikationsverlauf

Received 24 August 2011
Publikationsdatum:
27. Oktober 2011 (online)

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Abstract

Adducts of peptides and arylboronic acids are attractive tools for the selective recognition of carbohydrates. These structures resemble at least some of the properties of natural carbohydrate binders and have therefore been termed lectin mimetics or boronolectins. In this report, we describe the synthesis of appropriately functionalized benzoboroxoles as modular components for the assembly of boronolectins. These benzoboroxoles have been prepared in a few steps from readily available starting materials. In conclusion, versatile functionalized benzoboroxoles are reported that can be used for the construction of larger conjugates by peptide coupling or copper-mediated cycloadditions (click reactions) with azides.

Key words

carbohydrate recognition - boronic acids - click reactions - boronolectins - benzoboroxoles

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