Issue 30, 2021

Development of a multifunctional neoglycoside auxiliary for applications in glycomics research

Abstract

A novel, multifunctional, tetrazine-containing neoglycoside auxiliary has been synthesized in three steps and 28% overall yield. The oxyamine was conjugated with unprotected carbohydrates under aqueous conditions (pH = 4.7), with DMF as a cosolvent, to provide neoglycosides in yields ranging between 51% and 68%. This auxiliary displayed broad advantages in the isolation and purification of complex carbohydrate mixtures, compatibility during extension by glycosyltransferases, and direct conjugation to chemical probes. Furthermore, the auxiliary can be removed in 96% yield under acidic conditions (0.25% TFA in H2O) that leave glycosidic linkages intact. Thereby, the tetrazine-containing neoglycoside auxiliary can serve to facilitate future glycomics investigations.

Graphical abstract: Development of a multifunctional neoglycoside auxiliary for applications in glycomics research

Supplementary files

Article information

Article type
Communication
Submitted
14 May 2021
Accepted
08 Jul 2021
First published
15 Jul 2021

Org. Biomol. Chem., 2021,19, 6613-6617

Development of a multifunctional neoglycoside auxiliary for applications in glycomics research

T. Cheewawisuttichai and M. Brichacek, Org. Biomol. Chem., 2021, 19, 6613 DOI: 10.1039/D1OB00941A

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