Issue 23, 2020

Synthesis of type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of l-[U-13C6]-fucose for NMR binding studies

Abstract

While 13C-labelled proteins are common tools in NMR studies, lack of access to 13C-labelled carbohydrate structures has restricted their use. L-Fucose is involved in a wide range of physiological and pathophysiological processes in mammalian organisms. Here, L-[U-13C6]-Fuc labelled type I Lewis b (Leb) structures have been synthesised for use in NMR binding studies with the Blood-group Antigen Binding Adhesin (BabA), a membrane-bound protein from the bacterium Helicobacter pylori. As part of this work, an efficient synthesis of a benzylated L-[U-13C6]-Fuc thioglycoside donor from L-[U-13C6]-Gal has been developed. The design and synthesis of an orthogonally protected tetrasaccharide precursor enabled controlled introduction of one or two 13C-labelled or non-labelled fucosyl residues prior to global deprotection. NMR analysis showed that it is straightforward to assign the anomeric centres as well as the H-5 positions to the individual fucosyl residues which are relevant for NMR binding studies.

Graphical abstract: Synthesis of type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of l-[U-13C6]-fucose for NMR binding studies

Supplementary files

Article information

Article type
Paper
Submitted
26 Feb 2020
Accepted
27 Mey 2020
First published
27 Mey 2020

Org. Biomol. Chem., 2020,18, 4452-4458

Synthesis of type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of L-[U-13C6]-fucose for NMR binding studies

M. Long, A. Ní Cheallaigh, M. Reihill, S. Oscarson and M. Lahmann, Org. Biomol. Chem., 2020, 18, 4452 DOI: 10.1039/D0OB00426J

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