Structure-activity relationships in carbohydrates revealed by their hydration

• Published in: Biochimica et biophysica acta. General subjects Vol. 1861; no. 6; pp. 1486 - 1493
• Main Authors: Maugeri, Laura, Busch, Sebastian, McLain, Sylvia E., Pardo, Luis Carlos, Bruni, Fabio, Ricci, Maria Antonietta
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01.06.2017
• Subjects: Carbohydrate Conformation; cellobiose; Cellobiose - chemistry; Cellobiose - metabolism; cellulosic fibers; Computer modelling; computers; glucose; Glucose - chemistry; Glucose - metabolism; Humans; Ligands; Models, Chemical; Molecular Docking Simulation; Neutron Diffraction; receptors; Receptors, G-Protein-Coupled - metabolism; Signal Transduction; Structure-Activity Relationship; structure-activity relationships; Structure-function relationship; Sweet taste; Taste; Taste Perception; trehalose; Trehalose - chemistry; Trehalose - metabolism; Water; Water - chemistry; Water-carbohydrates interactions; Water; Computer modelling; Sweet taste; Water-carbohydrates interactions; Neutron diffraction; Structure-function relationship
• ISSN: 0304-4165; 1872-8006
• DOI: 10.1016/j.bbagen.2016.12.017

One of the more intriguing aspects of carbohydrate chemistry is that despite having very similar molecular structures, sugars have very different properties. For instance, there is a sensible difference in sweet taste between glucose and trehalose, even though trehalose is a disaccharide that comprised two glucose units, suggesting a different ability of these two carbohydrates to bind to sweet receptors. Here we have looked at the hydration of specific sites and at the three-dimensional configuration of water molecules around three carbohydrates (glucose, cellobiose, and trehalose), combining neutron diffraction data with computer modelling. Results indicate that identical chemical groups can have radically different hydration patterns depending on their location on a given molecule. These differences can be linked with the specific activity of glucose, cellobiose, and trehalose as a sweet substance, as building block of cellulose fiber, and as a bioprotective agent, respectively. This article is part of a Special Issue entitled “Recent Advances in Bionanomaterials” Guest Editors: Dr. Marie-Louise Saboungi and Dr. Samuel D. Bader. •Hydration structure of carbohydrates can be used to predict biological function.•Characterization of water-carbohydrates interactions at the atomic scale.•Possible relevance for sweet taste response.