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Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors

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Title: Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors
Authors: Nakagita, Tomoya Browse this author
Ishida, Akiko Browse this author
Tachrim, Zetryana Puteri Browse this author
Wang, Lei Browse this author
Misaka, Takumi Browse this author →KAKEN DB
Hashimoto, Makoto Browse this author →KAKEN DB
Keywords: lactisole
photoaffinity label
sweet taste
Issue Date: Jun-2020
Publisher: MDPI
Journal Title: Molecules
Volume: 25
Issue: 12
Start Page: 2790
Publisher DOI: 10.3390/molecules25122790
Abstract: Lactisole, which has a 2-phenoxy propionic acid skeleton, is well-known as an inhibitor of sweet taste receptors. We recently revealed some of the structure-activity relationships of the aromatic ring and chiral center of lactisole. Photoaffinity labeling is one of the common chemical biology methods to elucidate the interaction between bioactive compounds and biomolecules. In this paper, the novel asymmetric synthesis of lactisole derivatives with common photophores (benzophenone, azide and trifluoromethyldiazirine) for photoaffinity labeling is described. The synthetic compounds are subjected to cell-based sweet taste receptors, and the substitution with trifluoromethyldiazirinyl photophore shows the highest affinity to the receptor of the synthesized compounds.
Type: article
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)

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