Bacterial cellulose-based hydrogels carrying Lewis X trisaccharides as a system for monitoring carbohydrate-carbohydrate interactions with the naked eye

Bacterial cellulose-based hydrogels carrying Lewis X trisaccharides as a system for monitoring carbohydrate-carbohydrate interactions with the naked eye

Bacterial cellulose-based hydrogels carrying Lewis X trisaccharides were prepared via a three-step synthetic route, involving (1) NaIO 4 oxidation of commercially available nata de coco, (2) reductive amination of the product using propargylamine, and (3) Cu + -catalysed alkyne-azide cycloaddition u...

Full description

Saved in:
Bibliographic Details
Published in:Journal of carbohydrate chemistry Vol. 42; no. 1-3; pp. 40 - 58
Main Authors: Dong, Jiayu, Hiroki, Katsunari, Tobito, Mizuki, Yoshida, Keisuke, Tanabe, Ai, Shindo, Taiki, Gunji, Megu, Li, Qintong, Hasegawa, Teruaki
Format: Journal Article
Language:English
Published: Philadelphia Taylor & Francis 24-03-2023
Taylor & Francis Ltd
Subjects:
Alkynes
Aqueous solutions
bacterial cellulose-based hydrogel
Calcium ions
Carbohydrate-carbohydrate interaction
Carbohydrates
Cellulose
Cycloaddition
Galactosides
Hydrogels
Lewis X trisaccharide
Oligosaccharides
Oxidation
self-assembly
visible size
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Bacterial cellulose-based hydrogels carrying Lewis X trisaccharides were prepared via a three-step synthetic route, involving (1) NaIO 4 oxidation of commercially available nata de coco, (2) reductive amination of the product using propargylamine, and (3) Cu + -catalysed alkyne-azide cycloaddition using azide-functionalised Lewis X trisaccharides. The resultant bacterial cellulose-based hydrogels were assembled in aqueous media containing Ca 2+ or Na + , demonstrating ion-mediated interactions among Lewis X trisaccharides. Furthermore, reference experiments using bacterial cellulose-based hydrogels carrying N-acetyl-lactosaminides and those carrying N-acetyl-D-glucosaminides revealed that the two non-reducing terminals (i.e., β-galactoside and α-fucoside of Lewis X trisaccharide) substantially contribute to their interactions.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2023.2242927