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A Solid-State NMR Application of the Anomeric Effect in Carbohydrates: Galactosamine, Glucosamine, and N-acetyl-glucosamine

A Solid-State NMR Application of the Anomeric Effect in Carbohydrates: Galactosamine, Glucosamine, and N-acetyl-glucosamine

Der-Lii M Tzou

Solid State Nucl Magn Reson. 2005 Jun;27(4):209-14.

PMID: 15799877

Abstract:

Simple 2D 13C/15N heteronuclear correlation solid-state NMR spectroscopy was implemented to resolve the 15N resonances of the alpha and beta anomers of three amino monosaccharides: galactosamine (GalN), glucosamine hydrochloride (GlcN), and N-acetyl-glucosamine (GlcNAc) labeled specifically with 13C1/15N spin pairs. Although the 15N resonances could not be distinguished in normal 1D spectra, they were well resolved in 2D double CP/MAS correlation spectra by taking advantage of the 13C spectral resolution. The alpha and beta resonances shifted apart by 3-5 ppm in their 13C chemical shifts, and differed by 1-2 ppm in the extended 15N dimension. Aside from this, the detection of other 13C/15N correlations over short distances was also achieved arising from the C2, C3 and CO carbons present in natural abundance. 2D double CP/MAS chemical shift correlation NMR spectroscopy is a simple and powerful technique to characterize the anomeric effect of amino monosaccharides. Applications of the 2D method reveal well-resolved 15N and 13C chemical shifts might be useful for structural determination on carbohydrates of biological significance, such as glycopeptide or glycolipids.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42410455	Kevetrin-(4-isothioureido-13C,15N2-butyronitrile-13C,15N) hydrochloride			Price

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