High‐Resolution 1H‐NMR Spectroscopy of Free and Glycosidically Linked O‐ Acetylated Sialic Acids
Open Access
- 1 February 1982
- journal article
- research article
- Published by Wiley in European Journal of Biochemistry
- Vol. 122 (2), 305-311
- https://doi.org/10.1111/j.1432-1033.1982.tb05881.x
Abstract
A number of naturally occurring and synthetic, partially O-acetylated derivatives of N-acetylneuraminic and N-glycoloylneuraminic acids have been investigated by 360-MHz 1H-NMR spectroscopy. O-Acetylation causes strong downfield shifts for the resonances of neighbouring sugar-skeleton protons. The chemical shifts of these resonances, together with their characteristic multiplet shapes, can be used for localisation of the position of O-acetyl substituents in the molecule. The number of such substituents in the molecule can be inferred from the number of acetyl-methyl singlets, which also have characteristic resonance positions. This method for determination of the number and position of O-acetyl substituents in sialic acid residues is very powerful for structural analysis of underivatized carbohydrate chains derived from glycoconjugates. This is demonstrated for the oligosaccharide N-acetyl-4-O-acetylneuraminosyl-(α2→3)-lactose isolated from echidna milkThis publication has 28 references indexed in Scilit:
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