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Issue 19, 2021
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An efficient and scalable synthesis of 2,4-di-N-acetyl-l-altrose (l-2,4-Alt-diNAc)

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Abstract

Bacterial nonulosonic acids such as pseudaminic acids and others constitute a family of 9-carbon monosaccharides that contain a common 3-deoxy-2-ketoacid fragment but differ in their stereochemistries at 5 stereogenic centers between C-4 to C-8. Their unique structures make them attractive targets for use as antigens in vaccinations to combat drug-resistant bacterial infections and their challenging stereochemistries have attracted considerable attention from chemists. In this work we report the development of an improved synthesis for 2,4-di-N-acetyl-L-altrose (L-2,4-Alt-diNAc), which is a key hexose required for the chemical and chemoenzymatic synthesis of pseudaminic acids. Using L-fucose as a starting material, our synthesis overcomes several pitfalls in previously reported syntheses.

Graphical abstract: An efficient and scalable synthesis of 2,4-di-N-acetyl-l-altrose (l-2,4-Alt-diNAc)

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Article information


Submitted
08 Feb 2021
Accepted
12 Mar 2021
First published
19 Mar 2021

This article is Open Access

RSC Adv., 2021,11, 11583-11594
Article type
Paper

An efficient and scalable synthesis of 2,4-di-N-acetyl-L-altrose (L-2,4-Alt-diNAc)

A. Niedzwiecka, C. Sequeira, P. Zhang and C. Ling, RSC Adv., 2021, 11, 11583
DOI: 10.1039/D1RA01070K

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