Manipulation and magnification of the sweetness of sucrose

Abstract: Sweetness magnification of sucrose occurs when specific hydroxyls are replaced with chloro groups, particularly at carbons 4, l', 4 ' and 6, but not 6, rising progressively from 2- 20 times in mono-chlorides to>5000 times in tetra-chlorides. This surge in activity is interpreted by the formation of a sweetener-receptorcomplex, loosely linked by two H-bonds from 2-0 (B, ) and 3'-OH (AH,) of the sucrose derivative to the N-asparaginyl unit of an a-helical protein, which is strengthened by dispersive interactions with the side-chains of the receptor protein. These interactions increase in proportion with the degree of chloro-substitution in the sweet compounds, as illustrated by the molecular modelling by computer graphics.,The sweetness of sucrose (1, R=R,=OH), the conventional standard (lx), can be manipulated 'upwards or downwards in a variety of ways by using either additives or structural changes. Thus, caramel-type molecules, such as maltol or furaneol, enhance its sweetness by 10- 20 % (ref. 1) andso does synergism with H, I. sweeteners, especially aspartame, cyclamate, acesulphame and saccharin. Also, replacement of certain hydroxyl groups in sucrose by chloro groups can either enhance or r reduce its sweet taste, the 6-mono-chloride (1, R=CI, R,=OH) being virtually tasteless whilst th