Modeling the tyrosine–sugar interactions in supersonic expansions: glucopyranose–phenol clusters

• DOI: 10.1039/c6cp00560h
• Publication Date: 2016-03-14T16:32:48Z
• Authors: Imanol Usabiaga; Jorge González; Pedro F. Arnáiz; Iker León; Emilio J. Cocinero; José A. Fernández
• Keywords: Models, Molecular; Glucose; Phenol; Entropy; Carbohydrate Conformation; Tyrosine; 01 natural sciences; 0104 chemical sciences

Sugars are fundamental building blocks for living organisms and their interaction with proteins plays a central role in biological processes, such as energy storage production, post-transductional modifications or immune response. Understanding those processes require deep knowledge of the forces that drive interactions at molecular level. Here we explore between α/β-methyl-d-glucopyranose β-phenyl-d-glucopyranose phenol, chromophore tyrosine, using combination mass-resolved laser electronic spectroscopy supersonic expansions quantum mechanical calculations. The structures complexes detected jet stabilized by subtle equilibrium several types weak interactions, among which dispersion may tilt balance. In particular, small structural changes introduced orientation anomeric substituent amplified phenol. Consequently, number conformational isomers experimentally is different each system they present also differences preferred solvation site. Furthermore, inclusion entropic terms calculated advisable to understand energetic reasons detection set experimental isomers.