Synthesis of a Gal-β-(1→4)-Gal disaccharide as a ligand for the fimbrial adhesin UcaD
Eric D. Boittier A B , Norbert Wimmer A B , Alexandria K. Harris A B , Mark A. Schembri A B and Vito Ferro
A B *
+ Author Affiliations
- Author Affiliations
A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.
B Australian Infectious Diseases Research Centre, The University of Queensland, Brisbane, Qld 4072, Australia.
Australian Journal of Chemistry 76(1) 30-36 https://doi.org/10.1071/CH22158
Submitted: 10 July 2022 Accepted: 25 August 2022 Published: 8 December 2022
© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)
Abstract
The disaccharide Gal-β-(1→4)-Gal was recently identified as a ligand for the adhesin UcaD, a fimbrial protein used by Proteus mirabilis to adhere to exfoliated uroepithelial cells and colonise the urinary tract. To facilitate further studies, Gal-β-(1→4)-Gal was synthesised as the α-methyl glycoside via glycosylation of methyl 2,3,6-tri-O-benzoyl-α-d-galactopyranoside with 2,3,4,6-tetra-O-acetyl-d-galactopyranosyl trichloroacetimidate, followed by deprotection. The disaccharide was fully characterised by NMR spectroscopy. Earlier attempts to use a thiogalactoside as the glycosyl acceptor were hindered by intermolecular aglycone transfer side reactions.
Keywords: bacterial adhesins, disaccharide synthesis, galactopyranoside, Gal-β-(1→4)-Gal, glycosylation, intermolecular aglycone transfer, Proteus mirabilis, uropathogenic Escherichia coli.
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