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

Autor: Tomoya Nakagita, Akiko Ishida, Zetryana Puteri Tachrim, Lei Wang, Takumi Misaka, Makoto Hashimoto
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Molecules, Vol 25, Iss 12, p 2790 (2020)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules25122790
Popis: 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.
Databáze: Directory of Open Access Journals
Nepřihlášeným uživatelům se plný text nezobrazuje