Structure, sweetness and solution properties of small carbohydrate molecules

Abstract

The sweetness of small carbohydrate molecules in relation to their structure has been under investigation for several years. Tentative glucophores can now be assigned to some structures and the sweetness effect is thought to originate in a hydrogen bond between stimulus molecule and sweet receptor. A recent study of solution properties of small carbohydrates in relation to sweetness aims to examine the hydrogen bonding between water molecules and sweet solutes as a preliminary stage of taste chemoreception. Hydrated sugar molecules are presumed to accede to receptors before binding with the receptors is able to occur. Apparent molar and apparent specific volumes give indications of the effective size of sapid solute and its compatibility with water structure. Axial and equatorial hydroxy groups differ in their effects according to their location in the hexopyranose structure. Analogous structures exhibit analogous apparent molar volumes; these effects may be related to the differences of sweetness intensity between some sugar structures and the bitterness of othe;s. Although there is yet no simple relationship between sweetness intensity and apparent molar volume (4 V ) , it is possible that (OV) does govern the taste dominance of one molecular species in binary mixtures. Moreover, apparent specific volumes of a range of sapid solutes seem to correlate with taste quality.

Partial molar heat capacities and volumes of transfer of some saccharides from water to aqueous urea solutions atT= 298.15 K

“…Various experimental as well as theoretical (1)(2)(3)(74)(75)(76)(77)(78)(79)(80)(81)(82) attempts are underway to explore the correlation between the hydration characteristics of saccharides and their stereochemistry. The hydration of carbohydrates has been explained by invoking the concept of compatibility (between the water structure and carbohydrate molecules) through a specific hydration model.…”

Apparent molar volumes and 1H‐NMR relaxation values of glucose syrups

“…weight and structure (Birch and Shamil 1988;Shamil er To overcome some of the above problems, Kearsley a1 1989) and low-resolution pmr relaxation times (TI and 563…”

Structure–sweetness relationships for fructose analogs. Part III. 3-Deoxy-D-erythro-hexulose (3-deoxy-D-fructose): composition in solution and evaluation of sweetness

“…Interestingly, the examination of IR data led Mathlouthi and Portmann (12) to propose the same revised assignment. In 1988, on the basis of intensity-time studies of the sweetness of sugars, Birch et al (13,14) suggested that the anomeric center may play no direct role and that the AH-B component of the glycophore was the 3,4-a-glycol system. Very recently, Lichtenthaler and Immel (2) have defined and calculated molecular hydrophobicity potential profiles for sugars, which provide a global description of the hydrophilic and hydrophobic regions in the molecule.…”