SYNTHESIS OF AMINOACYL SUGAR DERIVATIVES AND THEIR TASTE CHARACTERISTICS. I. 2,3-DI- O-AMINOACYL DERIVATIVES OF ALKYL d-GLUCOPYRANOSIDES

Abstract

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

Design and synthesis of new sweeteners

“…First, the vicinal di-O-(L-aminoacyloxy) unit was a fundamental structural requirement, since substantial sweetness disappeared when one of the two aminoacyloxy residues was either eliminated or substituted by a D-aminoacyloxy unit. Second, the β-anomer of the sweet-tasting glycosides was not sweet, showing the requirement for the α-anomer [3]. Finally, regiospecific sweet taste induction was only observed in the 2,3-di-O-aminoacyl derivatives, and not in the 3,4-and 4,6-di-O-aminoacyloxy derivatives.…”