β-1-N-Benzamido-d-glucopyranose
15 Nov 1998-Acta Crystallographica Section C-crystal Structure Communications (International Union of Crystallography)-Vol. 54, Iss: 11, pp 1670-1672
TL;DR: In this paper, the pyranose ring adopts the 4C1(D) conformation and the N-acetyl group exists in the Z-anti conformation, the primary alcohol group is disordered between the two permitted orientations, gg and gt.
Abstract: In the title compound, 1-benzamido-β-d-glucopyranose, C13H17NO6, the pyranose ring adopts the 4C1(D) conformation and the N-acetyl group exists in the Z-anti conformation. The primary alcohol group is disordered between the two permitted orientations, gg and gt.
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TL;DR: An analysis of C-H)...O interactions in the crystal structures of all N-glycoprotein linkage region models and analogs reveals a cooperative network of bifurcated hydrogen bonds consisting of N-H...O and C-h...O interactions seen uniquely for the models.
Abstract: Elucidation of the intra- and intermolecular carbohydrate-protein interactions would greatly contribute toward obtaining a better understanding of the structure-function correlations of the protein-linked glycans. The weak interactions involving C-H...O have recently been attracting immense attention in the domain of biomolecular recognition. However, there has been no report so far on the occurrence of C-H...O hydrogen bonds in the crystal structures of models and analogs of N-glycoproteins. We present herein an analysis of C-H...O interactions in the crystal structures of all N-glycoprotein linkage region models and analogs. The study reveals a cooperative network of bifurcated hydrogen bonds consisting of N-H...O and C-H...O interactions seen uniquely for the models. The cooperative network consists of two antiparallel chains of bifurcated hydrogen bonds, one involving N1-H, C2'-H and O1' of the aglycon moiety and the other involving N2-H, C1-H and O1'' of the sugar. Such bifurcated hydrogen bonds between the core glycan and protein are likely to play an important role in the folding and stabilization of proteins.
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TL;DR: In this article, the pyranose ring adopts the 4C1(D) conformation and the N-acetyl group exists in the Z-anti conformation, the primary alcohol group is disordered between the two permitted orientations, gg and gt.
Abstract: In the title compound, 1-benzamido-β-d-glucopyranose, C13H17NO6, the pyranose ring adopts the 4C1(D) conformation and the N-acetyl group exists in the Z-anti conformation. The primary alcohol group is disordered between the two permitted orientations, gg and gt.