title: Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid.
abstract: The short syntheses of each of the mono-acetates of N-acetyl-D-neuraminic acid are reported. These are important molecules for studying the mechanism and function of enzymes which utilise Neu5Ac as a substrate. However, until now these molecules were not available as pure compounds and instead had to be studied as mixtures. Neu4,5Ac(2) and Neu5,8Ac(2) were synthesised from a common precursor in 2 and 4 steps respectively, while Neu2,4Ac(2) and Neu5,7Ac(2) were synthesised in 3 and 4 steps respectively from another common precursor. Both precursors could be easily prepared in 3 steps from Neu5Ac itself. Importantly, no scrambling of the anomeric stereochemistry was detected throughout the course of these syntheses.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, UK YO10 5DD. paul.clarke@york.ac.uk
authors.forename: Paul A
authors.initials: PA
authors.lastname: Clarke
authors.forename: Nimesh
authors.initials: N
authors.lastname: Mistry
authors.forename: Gavin H
authors.initials: GH
authors.lastname: Thomas
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000215:Acylation; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000085:Acetates; D019158:N-Acetylneuraminic Acid