De     novo synthesis and lectin binding studies of unsaturated carba-pyranoses

Timo Leermann; Oliver Block; Michael A. L. Podeschwa; Uwe Pfüller; Hans-Josef Altenbach

doi:10.1039/C003597A

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De novo synthesis and lectin binding studies of unsaturated carba-pyranoses†

Timo Leermann,*^a Oliver Block,^b Michael A. L. Podeschwa,^c Uwe Pfüller^d and Hans-Josef Altenbach^a

Author affiliations

* Corresponding authors

^a Bergische University Wuppertal, Gaussstrasse 20, Wuppertal, Germany
E-mail: timo.leermann@broteleermann.de
Fax: +49 (0)202 439 2648

^b Merck KGaA, Frankfurter Strasse 250, Darmstadt, Germany

^c Sanofi-Aventis, Industriepark Hoechst, Frankfurt, Germany

^d University Medical Center Hamburg, Zentrum für Experimentelle Medizin, Institut für Anatomie II, PhytoLab, Martinistrasse 52, Hamburg, Germany

Abstract

Starting from branched para-benzoquinones a practical and highly flexible route is described for the preparation of unsaturated carbapyranoses. The potential of the synthesized galactose analogues to act as competitive inhibitors in lectin-carbohydrate interactions is investigated by means of Surface Plasmon Resonance (SPR) Spectroscopy.

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Supplementary files

Synthetic procedures, NMR spectra and representative SPR binding sensorgrams PDF (1171K)

Article information

DOI: https://doi.org/10.1039/C003597A
Article type: Paper
Submitted: 26 Feb 2010
Accepted: 04 Jun 2010
First published: 30 Jun 2010

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Org. Biomol. Chem., 2010,8, 3965-3974

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De novo synthesis and lectin binding studies of unsaturated carba-pyranoses

T. Leermann, O. Block, M. A. L. Podeschwa, U. Pfüller and H. Altenbach, Org. Biomol. Chem., 2010, 8, 3965 DOI: 10.1039/C003597A

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Organic & Biomolecular Chemistry