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DOI: 10.1055/s-0043-1775405
Recent Progress in the Synthesis and Glycosylation of Rare Sugars
This work was supported by the Aarhus University Research Foundation (AUFF-E-2022-7-11) and the Novo Nordisk Foundation (NNF23OC0083957).
This Short Review is dedicated to Professor Erick M. Carreira on the occasion of his 60th birthday.
Abstract
Out of 42 naturally occurring monosaccharides, only seven are abundant in Nature (glucose, galactose, mannose, fructose, xylose, ribose, and l-arabinose), while the others have been classified as ‘rare sugars’. Fungi and bacteria use a wide range of monosaccharides, in contrast to mammals, reflected in their glycosylated metabolites, as well as the cellular machineries that are involved in their sugar metabolism. Recognition of the microbiome’s impact on human health has led to increased interest in microbial glycans, as they often mediate interaction between host and microbes. Efficient access to rare sugars and oligosaccharides is necessary to study their roles in Nature, which can provide new pharmacological leads. Furthermore, it enables the synthesis of bioactive glycosylated natural products and congeners. This short review highlights recent progress in the synthesis and the efficient, site- and stereoselective glycosylation of rare sugars. Finally, it provides a recent example where synthetic access to rare sugars has enabled biochemical studies to better understand and interfere with processes in Nature.
1 Introduction
2 Synthesis of Rare Sugars
2.1 Syntheses from Renewable Feedstock
2.2 De Novo Syntheses
3 Glycosylation
3.1 Catalyst-Controlled Glycosylation
3.2 One-Pot Iterative Oligosaccharide Synthesis in Solution
4 Application in Biochemical Research
5 Conclusion
Key words
carbohydrates - rare sugars - oligosaccharides - glycosylation - catalysis - photochemistryPublication History
Received: 16 April 2024
Accepted after revision: 02 September 2024
Article published online:
08 October 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
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