title: Structural relationships of sugars to taste.
abstract: Chemical modification of sugars and their simple analogues indicates that these types of compound are almost always sweet, bitter, or bitter/sweet; hence, the two basic tastes may be intimately associated features of the same molecule. Stepwise modification at each chiral center around the sugar ring allows the sapid functions in these molecules to be mapped and leads to the inescapable conclusion that sugar molecules may be "polarized" on taste bud receptors, so that one end of the molecule elicits sweetness and the other bitterness. However, more extensive chemical modification evidently causes the molecule to realign itself in entirely different ways on the receptor. In most oligosaccharides only one sugar residue is likely to bind to the taste receptor, and this is probably a nonreducing end group, because the anomeric center of glucopyranose types of structure does not appear to affect sweetness. Sweetness depresses bitterness and bitterness depresses sweetness. Hence, it is not possible to make structural comparisons between analogues without correcting for these effects. However, some semiquantitative studies have established the value of current hydrogen bond theories of sweetness and the ideal oxygen-oxygen interorbital spacings for sweetness criteria in sugar molecules.
mesh_terms: D000085:Acetates; D002241:Carbohydrates / Q000502:physiology*; D002599:Chalcone / Q000031:analogs & derivatives; D003511:Cyclohexanols; D003837:Deoxy Sugars; D004187:Disaccharides; D005632:Fructose; D006018:Glycols; D006027:Glycosides; D006801:Humans; D006860:Hydrogen Bonding; D007661:Ketoses; D008757:Methylglucosides; D008954:Models, Biological; D008968:Molecular Conformation; D009005:Monosaccharides; D011485:Protein Binding; D011984:Sensory Receptor Cells / Q000502:physiology; D013329:Structure-Activity Relationship; D013649:Taste / Q000502:physiology*; D014199:Trehalose / Q000031:analogs & derivatives
chemical_list: D000085:Acetates; D002241:Carbohydrates; D003511:Cyclohexanols; D003837:Deoxy Sugars; D004187:Disaccharides; D006018:Glycols; D006027:Glycosides; D007661:Ketoses; D008757:Methylglucosides; D009005:Monosaccharides; D005632:Fructose; D002599:Chalcone; D014199:Trehalose