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Full Paper
Carbamate Linker Strategy in Solid-Phase Synthesis of Amino-Functionalized Glycoconjugates for Attachment to Solid Surfaces and Investigation of Protein-Carbohydrate Interactions
Article first published online: 4 DEC 2008
DOI: 10.1002/ejoc.200800670
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Spjut, S., Pudelko, M., Hartmann, M. and Elofsson, M. (2009), Carbamate Linker Strategy in Solid-Phase Synthesis of Amino-Functionalized Glycoconjugates for Attachment to Solid Surfaces and Investigation of Protein-Carbohydrate Interactions. European Journal of Organic Chemistry, 2009: 349–357. doi: 10.1002/ejoc.200800670
Publication History
- Issue published online: 5 JAN 2009
- Article first published online: 4 DEC 2008
- Manuscript Received: 8 JUL 2008
Funded by
- Swedish Research Council
- J. C. Kempe Foundation
Keywords:
- Solid-phase synthesis;
- Glycoconjugates;
- Carbohydrates;
- Proteins;
- Carbohydrate protein interactions;
- Carbamate linker;
- Gel-phase 19F NMR spectroscopy;
- Microtiter plates
Graphical Abstract
Serine-based amino-functionalized neoglycolipids were prepared by solid-phase synthesis using a carbamate-linker strategy and monitoring with gel-phase 19F NMR spectroscopy. The terminal amine obtainedafter cleavage was conjugated to amino-functionalized microtiter plates using didecyl squarate and the array was successfully probed with a galactose-binding lectin.
Abstract
Amino-functionalized serine-based galactose and glucose neoglycolipids were prepared by solid-phase synthesis using a carbamate strategy for anchoring amino functionalities to a (2-fluoro-4-hydroxymethylphenoxy)acetic acid linker resin. Key synthetic steps were monitored with gel-phase 19F NMR spectroscopy. Cleavage from the solid support was performed with trifluoroacetic acid. The terminal amine of the neoglycolipids was conjugated with didecyl squarate and then immobilized in amino-functionalized microtiter plates and the glycoconjugates were successfully probed with a galactose-binding lectin.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)