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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 | | diazirine | | azide | | benzophenone |
| 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. |
| Rights: | http://creativecommons.org/licenses/by/4.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/79221 |
| 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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