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Nofre-Tinti E1 and E4 Sweetener Subsites Activity on High Sweetness of Chlorodeoxy Derivatives of Sucrose and Galactosucrose

Pietrzycki W.

Polish Journal of Chemistry

2002

Vol. 76 / nr 6

875-889

PM3 quantum chemical population analysis in the ground state was performed for sucrose and galactosucrose, their 8 chlorodeoxy derivatives and threonine as a moiety of sweet taste receptor. QSAR (Quantitative Structure-Activity Relationship) studies on RSj relative sweetness of these sugars is carried out based on calculated quantum chemical parameters derived from independent particle model. It excellently explains very high sweetness of 1_,4,6_-trichloro-1_,4,6_-trideoxy-galactosucrose (RSj = 2000), 1_,4,6,6_-tetrachloro-1_,4,6,6_-tetradeoxy-galactosucrose (RSj =1000) and other chlorosugars. Presented QSAR analysis brings rather a limited contribution of the G4(1_-CH2) and G1(6_-CH2) dispersion fructofuranose subsites to Nofre-Tinti sweetener and reveals a great activity of E4(Cl-1_) and E1(Cl-6_) charge-transfer fructofuranose subsites in this sweetener. The latter subsites have a character of strong n-electron donors. According to Brand and Feigin, such a property may result in substantial increase of probability of a stimulus-gated ion channel transduction scheme for sweet taste.