Abstract
Sialic acid (N -acetylneuraminic acid) is a carbohydrate that is often found on the ends of oligosaccharide
chains in biological systems. As such, it is important in several biological recognition/communication
events mediated by sialic acid recognising proteins that play integral roles in these
phenomena. It is therefore necessary to develop synthetic routes to sialic acid and
its derivatives and analogues. Many of these routes have led to compounds used as
enzyme inhibitors for treatment of disease states and also as probes of biologically
relevant binding events and of the mechanisms of enzyme action. Every position on
the nine-carbon backbone of sialic acid has been derivatised for such purposes, being
synthesised both chemoenzymatically and chemically from precursors ranging from non-carbohydrate
sources to sialic acid itself. This review describes various synthetic strategies
developed for the synthesis of sialic acid and its variants at each position on the
carbon skeleton.
1 Introduction
2 Naturally Occurring Variants
3 Synthesis of Sialic Acid
3.1 Enzymatic Syntheses
3.2 Chemical Syntheses
4 Substituted Sialic Acid Analogues
4.1 Substitution at C1
4.2 Variation at C3
4.3 Modification at C4
4.4 Amide Variation at C5
4.5 Modification at C6
4.5.1 Substitution of the Ring Oxygen
4.5.2 Substitution of the Glycerol Side Chain
4.6 Modifications at C7, C8, and C9
5 Conclusions
Key words
carbohydrates - organometallic reagents - ozonolysis - stereoselectivity - sialic
acids
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