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Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations

Willén, Daniel LU ; Mastio, Roberto LU ; Söderlund, Zackarias LU orcid ; Manner, Sophie LU ; Westergren-Thorsson, Gunilla LU orcid ; Tykesson, Emil LU orcid and Ellervik, Ulf LU orcid (2021) In Bioconjugate Chemistry 32(12). p.2507-2515
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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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Bioconjugate Chemistry
volume
32
issue
12
pages
2507 - 2515
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:34784477
  • scopus:85119925036
ISSN
1043-1802
DOI
10.1021/acs.bioconjchem.1c00473
project
Small molecules that interfere with the biosynthesis of dermatan sulfate for exploration of cell surface carbohydrates and use as cancer therapy
language
English
LU publication?
yes
id
a7483bad-320b-4084-a6da-ed90f8b7646e
date added to LUP
2021-12-14 14:16:44
date last changed
2025-01-13 19:55:34
@article{a7483bad-320b-4084-a6da-ed90f8b7646e,
  abstract     = {{<p>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. </p>}},
  author       = {{Willén, Daniel and Mastio, Roberto and Söderlund, Zackarias and Manner, Sophie and Westergren-Thorsson, Gunilla and Tykesson, Emil and Ellervik, Ulf}},
  issn         = {{1043-1802}},
  language     = {{eng}},
  number       = {{12}},
  pages        = {{2507--2515}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Bioconjugate Chemistry}},
  title        = {{Azide-Functionalized Naphthoxyloside as a Tool for Glycosaminoglycan Investigations}},
  url          = {{http://dx.doi.org/10.1021/acs.bioconjchem.1c00473}},
  doi          = {{10.1021/acs.bioconjchem.1c00473}},
  volume       = {{32}},
  year         = {{2021}},
}