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Updated: Jan 4, 2026

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
Comparative Study on the Effects of Picoloyl Groups in Sialylations Based on Their Substitution Pattern
Bradley Jones1, Alexanndra Behm1, Melanie Shadrick1
1Department of Chemistry , Southern Illinois University Edwardsville , 1 Hairpin Dr. , Edwardsville , Illinois 62025 , United States.
Abstract:
A novel 8-O-picoloylated sialyl donor has been developed, and the performance of various picoloylated sialyl donors in glycosylations with primary glycosyl acceptors has been evaluated. 8-O-Picoloyl and 4,9-di-O-picoloyl sialyl donors produced moderate to excellent yields of disaccharides with complete α-stereoselectivities. Synergistic effects between picoloyl and the accompanying O-protecting groups (benzoyl vs acetyl) were evaluated, as well as the effects of triflic acid concentration on the 8-O-picoloyl donor. 1H NMR analysis was also carried out to assess differences in the hydrogen-bonding net between sialyl donors.
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