Molecular Design of Sweet Tasting Compounds Based on 3β-Amino-3β-deoxy-18β-glycyrrhetinic Acid: Amido Functionality Eliciting Tremendous Sweetness

Abstract

A series of 18β-glycyrrhetinic acid (GA)-based, sweet tasting compounds has been prepared, where anionic NHCO(CH₂)_nCO₂K side chains are attached to the 3β-C position of the GA skeleton through an amide linkage. As compared with the corresponding ester-linking compounds, these amido-linking ones, except that of n = 0, elicit 13 to 25 times increase in sweetness. The sweetness enhancement is due probably to the proton donation capability of the amido NH group which would render the binding of these compounds to the taste bud cell receptor advantageous.