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

• Record Type: Journal Article
• Authors: Niedzwiecka, Anna; Sequeira, Carita; Zhang, Ping; Ling, Chang-Chun
• Is Part Of: RSC advances. Volume 11:Issue 19(2021)
• Page Start: 11583
• Page End: 11594
• Publication Date: 2021-03-19
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1ra01070k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : An efficient and scalable synthesis of pseudaminic acid precursor l -2, 4-Alt-diNAc was developed from l -fucose. The desired l -altro configuration and N -acetamido substitutions ensued from a sequence of highly regio- and stereoselective transformations. 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.