Versatile strategy for the synthesis of biotinlab

Authors: F Javier Muñoz Ángel Rumbero José V Sinisterra J Ignacio Santos Sabine André HansJ Gabius Jesús JiménezBarbero María J Hernáiz

Publish Date: 2008/03/18

Volume: 25, Issue: 7, Pages: 633-646

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Abstract

The emerging role of glycans as versatile biochemical signals in diverse aspects of cellular sociology calls for establishment of sensitive methods to monitor carbohydrate recognition by receptors such as lectins Most of these techniques involve the immobilization of one of the binding partners on a surface eg atomic force microscopy glycan array and Surface Plasmon Resonance SPR hereby simulating cell surface presentation Here we report the synthesis of fluorescent glycoconjugates with a functionalization strategy which avoids the frequently occurring ring opening at the reducing end for further immobilization on a surface or derivatization with biotin In order to improve the versatility of these derivatized glycans for biological studies a new approach for the synthesis of biotinylated and fluorescent glycans has also been realized Finally to illustrate their usefulness the neoglycoconjugates were immobilized on different surfaces and the interaction analysis with a model lectin the toxin from mistletoe proved them to act as potent ligands underscoring the merit of the presented synthetic approachThis work was supported by a Research Project of the MEC Ministerio de Educación y Ciencia de España CTQ200609052/BQU a European Project FP62003NMPSMF3 proposal 0117742 an EC Marie Curie Research Training Network grant MRTNCT2005019561 the research initiative LMUexcellent and one of the authors F Javier Muñoz thanks the MEC for a PhD grant MECFPU predoctoral fellowship AP20034820

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