460732-36-9Relevant academic research and scientific papers
Synthesis of aminoacyl sugar derivatives and their taste characteristics. I. 2,3-Di-O-aminoacyl derivatives of alkyl D-glucopyranosides
Machinami, Tomoya,Iibuchi, Norihiro,Nomura, Takushi,Mitsumori, Takeshi,Suami, Tetsuo,Hough, Leslie
, p. 131 - 142 (2007/10/03)
Aminoacyl derivatives of methyl α- and β-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 α-D-glucopyranoside showed a strong sweet taste (16-35x sucrose), which decreased of 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-(L-alanyl) derivatives of methyl D-glucopyranoside, the α-anomer was very sweet (16-25x suc.) whereas the β-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 α-configuration at C-1. Its α-isopropyl anomer showed the highest sweetness (64x suc.), hence the increased lipophilicity is also an important criterion.
