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Updated: Jul 20, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

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Published on: February 16, 2018

Hydroxamate-directed access to β-Kdo glycosides.

Sourav Pramanik¹, Soumik Mondal¹, Alexander Chinarev²

¹Department of Biological and Synthetic Chemistry, Centre of Biomedical Research (CBMR), Lucknow 226014, India.

Chemical Communications (Cambridge, England)

|August 1, 2023

Summary

Researchers developed a new method for synthesizing beta-Kdo glycosides using novel Kdo-glycosyl donors. This approach offers a highly effective route to stereoselectively produce these important carbohydrate structures.

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

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Published on: May 27, 2015

Area of Science:

Carbohydrate Chemistry
Organic Synthesis
Glycosylation

Background:

Transient aziridinone and azaoxyallyl cations are key intermediates in organic synthesis.
Hydroxamates offer unique reactivity compared to traditional amides in certain reactions.

Purpose of the Study:

To extend the reaction repertoire of α-halohydroxamates for glycosyl donor design.
To achieve stereoselective synthesis of β-Kdo glycosides.
To elucidate the role of the hydroxamate moiety in glycosylation reactions.

Main Methods:

Designing novel Kdo-glycosyl donors by installing a hydroxamate moiety at the anomeric center.
Utilizing the reactivity of α-halohydroxamates for generating reactive intermediates.
Performing control experiments to compare hydroxamate and amide functionalities.

Main Results:

The newly designed Kdo-glycosyl donors proved highly effective for glycosylation.
Stereoselective access to β-Kdo glycosides was achieved.
Control experiments highlighted the crucial role of the hydroxamate group over the amide group.

Conclusions:

The installation of a hydroxamate moiety at the anomeric center of Kdo derivatives is a viable strategy for creating effective glycosyl donors.
This method provides a stereoselective route to β-Kdo glycosides.
Hydroxamates are superior to amides in this specific glycosylation context.