Seventeen carbosulphamates (eight syqthesised in this study) and 23 heterosulphamates (seven synthesised here) have been examined with a view to extending previously developed ' r 2 structuretaste relationships for sulphamates (RNHSO;).Measurements of defined parameters x, y, z, and V ( V = xyz) for R using Corey-Pauling-:'oltun space-filling models for the 17 carbosulphamates have shown that their taste can be predicted in most cases using the previously developed semi-QSAR established. Predictions made from a recent pattern-recognition method study of sulphamate taste are shown to be partially incorrect.The heterosulphamates were also examined using CPK models and first-order molecular connectivity ( l x V ) measurements. The use of linear discriminant analysis on seven subsets of the five variables measured i.e. x, y, z, V, and 'xV showed that the subset, x, z, lxV misclassified only three of the 23 heterocompounds, i.e. the percentage misclassified was 13%.Mapping of the sulphamate receptor site on the basis of the measurements carried out suggests that the carbo-and hetero-sulphamstes use different sites to bind. This present work brings the database of taste-assessed sulphamates reported to over 1 20 compounds.
The effect of sulfamation on known tastants has been investigated using several series of compounds containing a primary amine function namely, nitroanilines, phenylureas and -thioureas and amino acids and peptides. Profund changes in taste took place on sulfamation. The effect of chirality on the taste portfolios of various sulfamates has also been examined by preparing sets of enantiomeric pairs from aliphatic, aliphatic/aromatic and alicyclic/aromatic precursor amines and aminoalcohols. Some interesting taste differences have emerged, though these are not as great as observed in the first study.530
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