No abstract

Sweet taste induction by alkyl 2,3-di-O-(L-aminoacyloxy)-α-D-glucopyranosides requires a combination of hydrophobic α-alkoxy and hydrophilic vicinal, diequatorially oriented, L-aminoacyloxy units. Pyranoside chair conformations afford the preferred stereochemical arrangements of these residues for optimum interaction with the receptor. For the design of new sweeteners based on sweetness inhibitors,

Aminoacyl derivatives of methyl a-and b-D-glucopyranosides have been synthesized in order to ascertain the structural features required for the perception of a sweet taste. 2,3-Di-O-(L-aminoacyl) derivatives of methyl a-Dglucopyranoside showed a strong sweet taste (16 -35Â sucrose), which decreased or disappeared when either one of the two L-aminoacyl groups was absent or substituted by a D-aminoacyl group. In the case of 2,3-di-O-(Lalanyl) derivatives of methyl D-glucopyranoside, the a-anomer was very sweet (16 -25Â suc.) whereas the b-anomer was not sweet. The structural prerequisite for sweetness in this group of compounds proved to be the presence of L-aminoacyl groups at C-2 and C-3, and the a-configuration at C-1. Its a-isopropyl anomer showed the highest sweetness (64Â suc.), hence the increased lipophilicity is also an important criterion. * Corresponding

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