Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations

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

doi:10.1021/acs.bioconjchem.1c00473

Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations

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

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	2507-2515
Journal	Bioconjugate Chemistry
Volume	32
Issue number	12
Early online date	2021
DOIs	https://doi.org/10.1021/acs.bioconjchem.1c00473
Publication status	Published - 2021

Subject classification (UKÄ)

Biochemistry and Molecular Biology
Medical Biotechnology

Access to Document

10.1021/acs.bioconjchem.1c00473

2 Doctoral Thesis (compilation)

Engineering the extracellular matrix to model diseases and orchestrate regeneration
Söderlund, Z., 2023, Lund: Lund University, Faculty of Medicine. 66 p.
Research output: Thesis › Doctoral Thesis (compilation)

Open Access
File
Tools for understanding the glycosaminoglycan biosynthesis
Willén, D., 2021, Lund: Lund University, Faculty of Science, Department of Chemistry, Centre for Analysis and Synthesis. 204 p.
Research output: Thesis › Doctoral Thesis (compilation)

File

1 Active

DSepi1: Small molecules that interfere with the biosynthesis of dermatan sulfate for exploration of cell surface carbohydrates and use as cancer therapy
Ellervik, U. (Researcher), Tykesson, E. (Researcher), Malmström, A. (Researcher) & Mastio, R. (Research student)
2014/01/01 → …
Project: Research

Cite this

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title = "Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations",

abstract = "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. ",

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doi = "10.1021/acs.bioconjchem.1c00473",

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AU - Willén, Daniel

AU - Mastio, Roberto

AU - Söderlund, Zackarias

AU - Manner, Sophie

AU - Westergren-Thorsson, Gunilla

AU - Tykesson, Emil

AU - Ellervik, Ulf

PY - 2021

Y1 - 2021

N2 - 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.

AB - 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.

U2 - 10.1021/acs.bioconjchem.1c00473

DO - 10.1021/acs.bioconjchem.1c00473

M3 - Article

C2 - 34784477

AN - SCOPUS:85119925036

SN - 1043-1802

VL - 32

SP - 2507

EP - 2515

JO - Bioconjugate Chemistry

JF - Bioconjugate Chemistry

IS - 12

ER -

Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations

Abstract

Subject classification (UKÄ)

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Research output

Engineering the extracellular matrix to model diseases and orchestrate regeneration

Tools for understanding the glycosaminoglycan biosynthesis

Projects

DSepi1: Small molecules that interfere with the biosynthesis of dermatan sulfate for exploration of cell surface carbohydrates and use as cancer therapy

Cite this