A QSPR Study of Sweetness Potency Using CODESSA Program

Alan R. Katritzky, Ruslan Petrukhin, Subbu Perumal, Mati Karelson, Indra Prakash and Nitin Desai

Abstract

A total of 396 natural and artificial comprehensively referenced sweeteners were classified by their structures into nine sets. The sweetness potencies were correlated with quantum chemical and other molecular descriptors using the heuristic and the best multi-linear regression methods of the CODESSA software package. QSPR models (two-parameter unless otherwise indicated) emerged for each subclass of sweeteners with R² values of  (i) 0.835 for 47 aldoximes, (ii) 0.959 for 8 acesulfamates, (iii) 0.927 for 9 sulfamates, (iv) 0.941 for 10 -arylsulfonylalkanoic acids, (v) 0.715 for 27 guanidines (0.802 in a three-parameter correlation), (vi) 0.769 for 30 ureas/thioureas (0.888 in a three-parameter correlation), (vii) 0.905 for 20 natural sweeteners, (viii) 0.957 for 7 miscellaneous sweeteners (one- parameter correlation), and (ix) 0.688 for 87 peptides (five-parameter correlation). A significant global five-parameter QSPR theoretical model with R² of 0.686 for the entire set of sweeteners is presented and discussed with reference to the possible existence of single or multiple sweetness receptors.