Examination of the effect of structural variation on the N-glycosidic torsion (ΦN) among N-(β-d-glycopyranosyl)acetamido and propionamido derivatives of monosaccharides based on crystallography and quantum chemical calculations
| Autor: | Duraikkannu Loganathan, Anne Imberty, Udayanath Aich, Mohamed Mohamed Naseer Ali, Serge Pérez |
|---|---|
| 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) |
| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
conformation
Models Molecular Glycosidic torsions Computational studies Crystal structure Crystallography X-Ray 01 natural sciences Biochemistry Analytical Chemistry quantum chemistry Pendent groups Acetamides Moiety Quantum chemical calculations Glycosides ComputingMilieux_MISCELLANEOUS chemistry.chemical_classification Crystallography chemical interaction Chemistry Hydrogen bond Torsion angles Glycosidic linkages Monosaccharides Eukaryota acetamide derivative General Medicine Mineralogy Intra-molecular interactions Torsional stress priority journal Computational chemistries Amino acids crystal structure glycosidation Stereochemistry Carbohydrates Glycosylated Dihedral angle 010402 general chemistry Quantum chemistry Hydrogen bonds Environmental factors monosaccharide Monosaccharide Conformational preferences Glycoproteins hydrogen bond 010405 organic chemistry Molecular packings Organic Chemistry Glycosidic bond X ray crystallography Crystallographic studies Structural variations Amides 0104 chemical sciences Glucose propionamide derivative hydrogen Intramolecular force Acetamido Sugar (sucrose) chemical structure Quantum Theory N-Glycoprotein Sugars |
| Zdroj: | Carbohydrate Research Carbohydrate Research, Elsevier, 2009, pp.355-361 |
| ISSN: | 0008-6215 |
| Popis: | GlcNAc?Asn linkage is conserved in the N-glycoproteins of all eukaryotes. l-Glutamine (Gln), which is a one carbon higher homolog of Asn, is never glycosylated. X-ray crystallographic study of several ?-1-N-acetamido- and propionamido derivatives of monosaccharides has earlier shown that the N-glycosidic torsion, ?N, is influenced to a larger extent by the structural variation of the sugar part than that of the aglycon moiety. In order to examine the influence of the carbohydrate pendent groups on the conformational preference of the N-glycosidic linkage with respect to ?N, several models and analogs with gluco and manno configuration have been studied in the present work by computational chemistry. The crystal structure of Xyl?NHPr is reported here and its molecular packing compared with related analogs. The conjunction of combining Crystallographic and computational studies allows to demonstrate the strong influence that the group at C2, and environmental factors particularly inter- and intramolecular interactions involving regular hydrogen bonds and the weak C-H���O contacts, have on the energy preference of the ?N torsion angle. � 2008 Elsevier Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
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