Carbamate Linker Strategy in Solid‐Phase Synthesis of Amino‐Functionalized Glycoconjugates for Attachment to Solid Surfaces and Investigation of Protein‐Carbohydrate Interactions

Abstract

AbstractAmino‐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)