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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.698-705
Published online, 7th July, 2014
DOI: 10.3987/COM-14-S(K)36
Synthesis of Photoreactive Diazirinyl Salicin Derivative to Elucidate Functional Analysis of the Bitter Taste Receptor

Munenori Sakurai, Takuma Yoshida, Lei Wang, Yuta Murai, Katsuyoshi Masuda, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, and Makoto Hashimoto*

*Division of Applied Science, Graduate School of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo, Hokkaido 060-8589, Japan

Abstract

Salicin (salicyl alcohol glucoside) is a substance well known for its bitter taste. A photoreactive diazirinyl derivative of salicin will be utilized for the functional analysis of interactions between the bitter taste receptor and salicin. Glucosides of salicyl derivatives are more difficult than phenol derivatives that are unsubstituted at the ortho-position. A diazirinyl salicin derivative was synthesized at moderate yields by glucosidation of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and 2-hydroxy-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzaldehyde in the presence of a phase-transfer catalyst, nBuEt3NBr, followed by reduction and deprotection.