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Updated: Nov 14, 2025

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
A versatile approach to the synthesis of glycans containing mannuronic acid residues
Catherine Alex1, Satsawat Visansirikul, Alexei V Demchenko
1Department of Chemistry and Biochemistry, University of Missouri - St Louis, One University Boulevard, St Louis, MO 63121, USA. demchenkoa@umsl.edu.
Abstract:
Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked viaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.
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