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SYNTHESIS OF PHOTOREACTIVE DIAZIRINYL SALICIN DERIVATIVE TO ELUCIDATE FUNCTIONAL ANALYSIS OF THE BITTER TASTE RECEPTOR

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Title: SYNTHESIS OF PHOTOREACTIVE DIAZIRINYL SALICIN DERIVATIVE TO ELUCIDATE FUNCTIONAL ANALYSIS OF THE BITTER TASTE RECEPTOR
Authors: Sakurai, Munenori Browse this author
Yoshida, Takuma Browse this author
Wang, Lei Browse this author
Murai, Yuta Browse this author
Masuda, Katsuyoshi Browse this author →KAKEN DB
Sakihama, Yasuko Browse this author →KAKEN DB
Hashidoko, Yasuyuki Browse this author →KAKEN DB
Hatanaka, Yasumaru Browse this author →KAKEN DB
Hashimoto, Makoto Browse this author →KAKEN DB
Keywords: Diazirine
Photoaffinity Label
Salicin
Bitter Taste
Glucosidation
Issue Date: 1-Jan-2015
Publisher: Elsevier
Journal Title: Heterocycles
Volume: 90
Issue: 1
Start Page: 698
End Page: 705
Publisher DOI: 10.3987/COM-14-S(K)36
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-alpha-D-glucopyranosyl bromide and 2-hydroxy-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzaldehyde in the presence of a phase-transfer catalyst, nBuEt(3)NBr, followed by reduction and deprotection.
Type: article (author version)
URI: http://hdl.handle.net/2115/58538
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 橋本 誠

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