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Updated: Nov 28, 2025

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview
Daria Grzywacz1, Beata Liberek1, Henryk Myszka1
1Laboratory of Glycochemistry, Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland.
Abstract:
Saponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponins, and many of them exhibit various pharmacological properties. Herein, we present an overview of semisynthetic saponins syntheses-diosgenyl β-d-glycosaminosides (d-gluco and d-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different N-protecting groups and various reaction conditions used for their synthesis are presented. In addition, this paper demonstrates the possibilities of chemical modifications of diosgenyl β-d-glycosaminosides, associated with functionalisation of the amino group. These provide N-acyl, N-alkyl, N,N-dialkyl, N-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented.
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