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GSL Structure Analysis by ¹³C NMR

What Is ¹³C NMR Analysis and Their Application in GSL Research

Nuclear magnetic resonance (NMR) technology is used to investigate carbon, particularly carbon-13. It detects carbon atoms in organic compounds in the same way as proton NMR identifies hydrogen atoms. ¹³C NMR only detects the ¹³C isotope. Despite being far less sensitive than ¹H NMR, ¹³C NMR is frequently used to investigate organic and organometallic compounds.

Fig.1 Chemical structure and ¹H NMR and ¹³C NMR spectra of Ara2-Me. (Fujita, et al., 2011)

Galactosylceramide (GalCer) was the first glycosphingolipid (GSL) to be identified. It is one of the simplest glycolipids and one of the most prevalent compounds in the vertebrate brain. It is made up of a single galactose residue linked to the C-1 hydroxyl group of ceramide, a lipid molecule.

Fig.2 Structure of glycosphingolipid. (Chiricozzi, 2021)

¹³C NMR Analysis Service at CD BioGlyco

Because ¹³C resonances have a wider chemical shift dispersion (δC ~15-180 ppm), the overlap problem is less severe. NMR chemical shifts of ³¹P resonances from ~10 to -5 ppm are often reported in carbohydrates, while ¹⁵N resonances can be observed at δN ~30-125 (spectral region of amine, N-sulfate, and amide groups). In heteronuclear correlation investigations, proton detection is frequently favored for the study of carbohydrates at natural isotope abundance over the direct recording of 1D ¹³C and ³¹P NMR spectra due to the better sensitivity of proton nuclei. ¹³C NMR chemical shifts of common aldohexopyranoses are presented in Fig.3.

Fig.3 Plots of ¹³C NMR chemical shifts of common aldohexopyranoses. (Fontana & Widmalm, 2023)

CD BioGlyco has established a well-equipped platform for the structural detection and analysis of polysaccharides. We provide customized GSL structural analysis services, including NMR-based Analysis and MS-based Analysis, depending on the needs of our clients. We provide ¹³C NMR analysis services operated by professional laboratory personnel and reported by a team of scientists dedicated to providing the best experience for our clients.

Fig.4 Standard analysis process at CD BioGlyco. (CD BioGlyco)

Advantages of Us

We provide custom ¹³C NMR analysis services, especially for polysaccharides, such as GSL, etc.
We will evaluate clients' needs, recommend suitable services, and work to provide customized solutions for our clients.
Our scientific team has extensive experience in glyco-chemistry, and our professional laboratory staff can complete our experimental protocols well.

CD BioGlyco has extensive expertise in the study of glycans. Our research and service team offers suitable and customized ¹³C NMR analysis services to our clients. If you are interested in our service, please feel free to contact us for further information.

References

Fujita, K.; et al. Molecular cloning and characterization of a β-L-arabinobiosidase in Bifidobacterium longum that belongs to a novel glycoside hydrolase family. Journal of Biological Chemistry. 2011, 286(7): 5143–5150.
Chiricozzi, E. Plasma membrane glycosphingolipid signaling: A turning point. Glycoconjugate Journal. 2021, 39(1): 99–105.
Fontana, C.; Widmalm, G. Primary structure of glycans by NMR spectroscopy. Chemical Reviews. 2023, 123(3): 1040–1102.

This service is for Research Use Only, not intended for any clinical use.