4276-73-7Relevant articles and documents
HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases
Charushin, V. N.,Chulakov, E. N.,Krasnov, V. P.,Levit, G. L.,Sadretdinova, L. Sh.,Tumashov, A. A.,Vakarov, S. A.
, p. 900 - 907 (2021/06/07)
The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.
Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor
Nakagita, Tomoya,Matsuya, Takumi,Narukawa, Masataka,Misaka, Takumi,Kobayashi, Takuya,Ishida, Akiko,Hashimoto, Makoto,Hirokawa, Takatsugu
, (2019/04/13)
Lactisole, an inhibitor of the human sweet taste receptor, has a 2-phenoxypropionic acid skeleton and has been shown to interact with the transmembrane domain of the T1R3 subunit (T1R3-TMD) of the receptor. Another inhibitor, 2,4-DP, which shares the same molecular skeleton as lactisole, was confirmed to be approximately 10-fold more potent in its inhibitory activity than lactisole; however the structural basis of their inhibitory mechanisms against the receptor remains to be elucidated. Crystal structures of the TMD of metabotropic glutamate receptors, which along with T1Rs are categorized as class C G-protein coupled receptors, have recently been reported and made it possible to create an accurate structural model for T1R3-TMD. In this study, the detailed structural mechanism underlying sweet taste inhibition was characterized by comparing the action of lactisole on T1R3-TMD with that of 2,4-DP. We first performed a series of experiments using cultured cells expressing the sweet taste receptor with mutations and examined the interactions with these inhibitors. Based on the results, we next performed docking simulations and then applied molecular dynamics-based energy minimization. Our analyses clearly revealed that the (S)-isomers of both lactisole and 2,4-DP, interacted with the same seven residues in T1R3-TMD and that the inhibitory potencies of those inhibitors were mainly due to stabilizing interactions mediated via their carboxyl groups in the vertical dimension of the ligand pocket of T1R3-TMD. In addition, 2,4-DP engaged in a hydrophobic interaction mediated by its o-Cl group, and this interaction may be chiefly responsible for the higher inhibitory potency of 2,4-DP.
Alkali-sensitive ring opening cucurbituril and application thereof
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Paragraph 0017; 0018, (2018/08/04)
The invention discloses alkali-sensitive ring opening cucurbituril. A structural formula of the alkali-sensitive ring opening cucurbituril is shown. The alkali-sensitive ring opening cucurbituril hasthe advantages that the alkali-sensitive ring opening cucurbituril can be used as a supermolecular medicine carrier and is provided with large ring cryptand with inner cavities, the ring rigidity of large rings can be reduced by means of ring opening, and accordingly the alkali-sensitive ring opening cucurbituril is extremely high in host-guest bonding capacity; the alkali-sensitive ring opening cucurbituril is excellent in alkali sensitivity, contains carboxylic acid groups and can be used as the medicine carrier to be widely applied to medicine delivery paths, and the water solubility and the stability of insoluble medicines can be greatly improved; the alkali-sensitive ring opening cucurbituril can be used as an alkali-sensitive carrier, medicines can be released in alkaline environments such as small intestines in human bodies, accordingly, effects of releasing the medicines in a sustained and controlled manner can be realized, and irritation of the medicines on gastric mucosas canbe prevented.