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Glycobiology Advance Access published online on December 12, 2005
Glycobiology, doi:10.1093/glycob/cwj070
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© The Author 2005. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org
Received October 21, 2005
Revised November 29, 2005
Accepted December 9, 2005

Article

Observation of a unique pattern of bifurcated hydrogen bonds in the crystal structures of the N-glycoprotein linkage region models

Duraikkannu Loganathan 1 * and Udayanath Aich 1

1 Department of Chemistry, Indian Institute of Technology Madras Chennai - 600036, INDIA

* To whom correspondence should be addressed.
Duraikkannu Loganathan, E-mail: loganath{at}iitm.ac.in


  Abstract

Elucidation of the intra- and intermolecular carbohydrate-protein interactions would greatly contribute toward obtaining a better understanding 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 anti-parallel chains of bifurcated hydrogen bonds, one involving N1-H, C2’-H & O1’ of the aglycon moiety and the other involving N2-H, C1-H & 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.

Keywords: Carbohydrates/C-H...O Interactions/N-Glycoprotein models & analogs/H Bonding/X-ray diffraction.
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