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STRUCTURAL FUNCTIONS AND TASTE IN THE SUGAR SERIES: THE STRUCTURAL BASIS OF BITTERNESS IN SUGAR ANALOGUES

1976; Wiley; Volume: 41; Issue: 6 Linguagem: Inglês

10.1111/j.1365-2621.1976.tb01182.x

1750-3841

G. G. Birch, C. K. Lee,

Advanced Chemical Sensor Technologies

ABSTRACT Chemical modification of simple sugars and glycosides almost always results in products which are bitter, sweet, or bitter/sweet, although they are occasionally tasteless. Bitterness in all these molecules appears to be the result of polar as well as lipophilic molecular features. Ring size and shape also play a part in the bitter response. Unlike sweetness which seems primarily to be associated with the third and fourth hydroxyls of glucopyranosyl structures, bitterness is chiefly associated with hydroxyl groups on carbon atoms 1, 2 and 6, and with the ring oxygen atom. The configuration of substituents on carbon atoms 1 and 2 may determine bitterness in many molecules and indeed β‐glycosides and β‐linked oligosaccharides are more likely to be bitter than their α‐linked counterparts. Unlike sweetness, which requires precise molecular dimensions in glucopyranosyl structures, no distinct interorbital distances can yet be established for bitterness. However, AH,B systems may suffice to explain bitterness in some types of sugar analogue.