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Final Manuscript 201213.pdf (718.96 kB)

Synthesis of 4-O-Alkylated N-Acetylneuraminic Acid Derivatives

preprint
submitted on 14.12.2020, 07:23 and posted on 15.12.2020, 12:43 by Emil Johansson, Rémi Caraballo, Mikael Elofsson

N-acetyl neuraminic acid (Neu5Ac) is a densely functionalized nine-carbon monosaccharide. It ubiquitously decorates the surface of mammalian cells were it is found in terminal positions of glycolipids and glycoproteins. This important saccharide and natural analogs play important roles in a number of processes in health and disease. Despite this few Neu5Ac based therapeutics have been developed. To further study and understand the chemistry and biology of Neu5Ac efficient protocols for synthesis of the parent natural compounds as well as synthetic analogs are required. In the manuscript, we report investigation of alkylation reactions to produce selectively modified Neu5Ac with focus on position 4. The study provides insights in the reaction and we establish robust protocols that allow selective modification of Neu5Ac for use as tool compounds and starting points for drug discovery.

Funding

Knut and Alice Wallenberg Foundation grant (KAW; grant reference 2013.0019)

History

Email Address of Submitting Author

mikael.elofsson@umu.se

Institution

Umeå University

Country

Sweden

ORCID For Submitting Author

0000-0002-3219-4669

Declaration of Conflict of Interest

The authors declare no competing financial interest.

Version Notes

First version.

Exports