Mass spectrometry and /sup 13/C nuclear magnetic resonance spectroscopy of compounds modeling the glycopeptide linkage of glycoproteins
The properties of several compounds useful as models for three-dimensional conformational studies and the investigation of the chemical degradation of glycopeptide linkages both of the N- and O-glycosidic type are described. Using the method of differential chemical shift in H/sub 2/O and D/sub 2/O as solvents, the carbon NMR spectrum of N-acetylglucosaminylasparagine, 1-N-acetyl-..beta..-D-glucopyranosylamine, and 1-N-acetyl-2-acetamido-..beta..-D-glycopyranosylamine has been assigned. Electron impact mass spectra of the peracetylated derivatives of the latter two compounds show a peak apparently unique to glycopyranosylamides at m/e = 269, no analog of which is observed in the mass spectra of other peracetylated sugars. As models of the ..cap alpha..-O-glycosidic linkage, fully assigned carbon NMR spectra of ..cap alpha..-methyl-N-acetylgalactosamine (GalNAc), ..cap alpha..-methyl-3-O-methyl GalNAc, and -GlcNAc as well as the disaccharide Glc-..beta..-l ..-->.. 3 GalNAc are reported. Because certain anomalies in the chemical shifts and /sup 1/J/sub CH/ observed in the disaccharide and in O-glycosylated glycoproteins are not observed in the simple model compounds, they may result from conformational interactions in the glycopeptides.
- Research Organization:
- Illinois Inst. of Tech., Chicago
- OSTI ID:
- 5580578
- Journal Information:
- Anal. Biochem.; (United States), Vol. 119:2
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
GLUCOPROTEINS
MOLECULAR STRUCTURE
CARBON 13
DECOMPOSITION
GLYCOSIDES
MASS SPECTROSCOPY
NUCLEAR MAGNETIC RESONANCE
PEPTIDES
CARBOHYDRATES
CARBON ISOTOPES
CHEMICAL REACTIONS
EVEN-ODD NUCLEI
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
NUCLEI
ORGANIC COMPOUNDS
PROTEINS
RESONANCE
SACCHARIDES
SPECTROSCOPY
STABLE ISOTOPES
550201* - Biochemistry- Tracer Techniques