Original scientific paper

A QSPR Study of Sweetness Potency Using the CODESSA Program

Alan R. Katritzky ; Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, USA
Ruslan Petrukhin ; Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, USA
Subbu Perumal ; Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, USA
Mati Karelson ; Department of Chemistry, University of Tartu, Jakobi St. 2, Tartu 51014, Estonia
Indra Prakash ; The NutraSweet Company, 601 E. Kensington Rd., Mt. Prospect, IL 60056-1300, USA
Nitin Desai ; The NutraSweet Company, 601 E. Kensington Rd., Mt. Prospect, IL 60056-1300, USA

Abstract

A total of 397 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 0.835 for 47 aldoximes, 0.959 for 8 acesulfamates, 0.919 for 9 sulfamates, 0.941 for 10 α-arylsulfonylalkanoic acids, 0.715 for 27 guanidines (0.802 in a three-parameter correlation), 0.769 for 30 ureas/thioureas (0.888 in a three-parameter correlation), 0.905 for 20 natural sweeteners, 0.957 for 7 miscellaneous sweeteners (one-parameter correlation), 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.

Keywords

QSPR; sweetness; CODESSA; model; prediction; data-base of sweeteners; correlation

Hrčak ID:

127532

URI

https://hrcak.srce.hr/127532

Publication date:

3.6.2002.

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