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Appl. Chem. Vol. 74, No. 7, pp.
Pure and Applied Chemistry
Vol. 74, Issue 7
Isovanillyl sweeteners. From molecules to receptors*
Angela Bassoli, Lucio Merlini**, and Gabriella Morini
Dipartimento di Scienze Molecolari Agroalimentari,
Università di Milano, Via Celoria 2, 20133 Milano, Italy
Abstract: Systematic modification of the structure
of the sweet natural compound phyllodulcin, containing the isovanillyl
glucophoric group, led to the synthesis of about 120 compounds. Features
of the heterocyclic ring conferring high sweetness potency were identified.
A strong increase in sweetness was obtained by the introduction of sulfur
atoms in the ring and by separation of the enantiomers. Results of the
quantitative structureactivity relationship (QSAR) studies on
this series are reported. Application of the pseudoreceptor modeling
approach afforded a three-dimensional binding site model for isovanillyl
sweeteners. Extension of this methodology to a large group of structurally
diverse compounds, including the commonly used sweeteners, gave a general
pseudoreceptor for the sweet compounds, consisting of 16 amino acids.
This pseudoreceptor, which has the peculiarity of giving a semiquantitative
evaluation of the sweetness intensity, could be used as a valid tool
to model the ligandreceptor interactions and to suggest some clues
about the identification of a possible binding site once the receptor
protein(s) are obtained.
* A special topic issue on the
science of sweeteners.
** Corresponding author.
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