Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations.

Daniel Willén, Roberto Mastio, Zackarias Söderlund, Sophie Manner, Gunilla Westergren-Thorsson, Emil Tykesson, Ulf Ellervik

Bioconjugate chemistry 2021 Dec 15

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We present a xylosylated naphthoxyloside carrying a terminal azide functionality that can be used for conjugation using click chemistry. We show that this naphthoxyloside serves as a substrate for β4GalT7 and induces the formation of soluble glycosaminoglycan (GAG) chains with physiologically relevant lengths and sulfation patterns. Finally, we demonstrate its usefulness by conjugation to the Alexa Fluor 647 and TAMRA fluorophores and coupling to a surface plasmon resonance chip for interaction studies with the hepatocyte growth factor known to interact with the GAG heparan sulfate.

Citation

Daniel Willén, Roberto Mastio, Zackarias Söderlund, Sophie Manner, Gunilla Westergren-Thorsson, Emil Tykesson, Ulf Ellervik. Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations. Bioconjugate chemistry. 2021 Dec 15;32(12):2507-2515