Effect of distal sugars and interglycosidic linkage on the N-glycoprotein linkage region conformation: Synthesis and X-Ray crystallographic investigation of ?-1-N-alkanamide derivatives of cellobiose and maltose as disaccharide analogs of the conserved chitobiosylasparagine linkage
| Autor: | Duraikkannu Loganathan, Serge Pérez, Venkatachalam Ramkumar, Manoharan Mathiselvam |
|---|---|
| Přispěvatelé: | inconnu, Inconnu, Centre de Recherches sur les Macromolécules Végétales (CERMAV), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), Carret, Michèle |
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Cellobiose
Stereochemistry Molecular Sequence Data Disaccharide 010402 general chemistry Crystallography X-Ray 01 natural sciences Biochemistry chemistry.chemical_compound N-Acetylglucosamine Carbohydrate Conformation Moiety Maltose Molecular Biology ComputingMilieux_MISCELLANEOUS Glycoproteins chemistry.chemical_classification 010405 organic chemistry Glycosidic bond Cell Biology Carbohydrate Carbohydrate Sequence 0104 chemical sciences Crystallography chemistry Intramolecular force |
| Zdroj: | Glycoconjugate J. Glycoconjugate J., 2014, pp.71-87 |
| ISSN: | 2381-3652 |
| Popis: | The linkage region constituents, 2-deoxy-2-acetamido-?-D-glucopyranose (GlcNAc) and L-asparagine (Asn) are conserved in the N-glycoproteins of all eukaryotes. Elucidation of the structure and conformation of the linkage region of glycoproteins is important to understand the presentation and dynamics of the carbohydrate chain at the protein/cell surface. Earlier crystallographic studies using monosaccharide models and analogs of N-glycoprotein linkage region have shown that the N-glycosidic torsion, N, is more influenced by the structural variation in the sugar part than that of the aglycon moiety. To access the influence of distal sugar as well as interglycosidic linkage (? or ?) on the N-glycosidic torsion angles, cellobiosyl and maltosyl alkanamides have been synthesized and structural features of seven of these analogs have been characterized by X-ray crystallography. Comparative analysis of the seven disaccharide analogs with the reported monosaccharide analogs showed that the N value of cellobiosyl analogs deviate ~9 with respect to Glc?NHAc. In the case of maltosyl analogs, deviation is more than 18. These deviations indicate that the N-glycosidic torsion is influenced by addition of distal sugar as well as with respect to inter glycosidic linkage (? or ?); it is less influenced by changes occurring at the aglycon. The ?2 value of alkanamide derived from glucose, cellobiose and maltose exhibit a large range of variations (from 1.6 to -109.9). This large span of ?2 value suggests the greater degree of rotational freedom around C1?-C2? bond which is restricted in GlcNAc alkanamides. The present finding explicitly proved the importance of molecular architecture in the N-glycoproteins linkage region to maintain the linearity, planarity and rigidity. These factors are necessary for N-glycan to serve role in inter- as well as intramolecular carbohydrate-protein interactions. � 2013 Springer Science+Business Media New York. |
| Databáze: | OpenAIRE |
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