Structure-activity relationships in carbohydrates revealed by their hydration

Abstract

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 of monosaccharides studied by Raman scattering

“…When dissolved in water, glucose predominantly assumes a six‐member chair conformation with a natural proportion of its α to β anomers of 36:64 (Figure ). As a consequence, the Raman spectrum of the solution (reported in Figure a,b, Curve gw) is expected to show not only a broadening of the bands but also a splitting of some of them.…”

“…A commercially and physiologically relevant aspect of their function as nutrients is their degree of sweetness, which does not seem to be correlated with solution properties, such as, for instance, solubility or viscosity . In particular, the sweetness (relative to sucrose) of glucose and mannose is reported equal to 0.74 and 0.32 respectively, whereas that of fructose equals 1.1, although all three molecules share the same chemical formula (C 6 H 12 O 6 ).…”

“…Saccharides have several relevant biological functions, as nutrients, or protectants against severe environmental conditions, as for instance, low temperatures and/or drought. For this reason, their aqueous solutions have attracted great interest in physical and chemical researches (see previous studies for a representative, although not exhaustive bibliography). Nevertheless, an agreed view of several aspects of their interaction with water, and in particular, their affinity for hydrogen bonding (H‐bonding), is still missing.…”

New Detector Based on Composite of Carbon Nanotubes with Nanoparticles of Cobalt Oxide for Carbohydrates Analysis by HPLC with Reverse Pulsed Amperometric Detection

“…Carbohydrates are among the most important naturally occurring biomolecules, and are regarded a vital source of food in the food industry as well as a potential source of fuel in the fuel industry. 1 The outstanding properties and usefulness of carbohydrates in alternative energy and biomass have contributed to its growing importance among researchers in the area. These organic compounds represent the major component of biomass, and it is believed that around 20% of all manufactured chemicals will come from biomass by 2020.…”

Multivariate Determination of Total Sugar Content and Ethanol in Bioethanol Production Using Carbon Electrodes Modified with MWCNT/MeOOH and Chemometric Data Treatment

“…Ethanol analysis is important due to its vast application in many industries and biotechnological processes such as production of wine, beer, foodstuffs, cosmetics and pharmaceutical products . Sugars are among the most important naturally occurring biomolecules and are important to the food industry as well as being a potential source of fuels . Sugars (or carbohydrates) represent the major component of biomass and it is believed that around 20 % of all manufactured chemicals will be originated from biomass by 2025 .…”