Carbohydrate-aromatic interactions: A computational and IR spectroscopic investigation of the complex, methyl α-l-fucopyranoside · toluene, isolated in the gas phase
Su Z., Cocinero EJ., Stanca-Kaposta EC., Davis BG., Simons JP.
A carbohydrate-aromatic complex, methyl α-l-fucopyranoside · toluene, which provides a model for probing the physical basis of carbohydrate-protein 'stacking' interactions, has been created in a molecular beam and probed through IR ion dip spectroscopy in the CH and OH regions. The results are interpreted in the light of DFT calculations using the MO5-2X functional. They indicate the creation of stacked structures with the aromatic molecule bonded either to the upper or to the lower face of the pyranoside ring, through CH3,4-π (upper) or CH1-π (lower) interactions leading to binding energies ≤18 kJ mol-1. © 2009 Elsevier B.V. All rights reserved.