Preparation of domoic acid analogues using a bioconversion system, and their toxicity in mice was written by Maeno, Yukari;Kotaki, Yuichi;Terada, Ryuta;Hidaka, Masafumi;Cho, Yuko;Konoki, Keiichi;Yotsu-Yamashita, Mari. And the article was included in Organic & Biomolecular Chemistry in 2021.Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate The following contents are mentioned in the article:
Domoic acid (1, DA), a member of the natural kainoid family, is a potent agonist of ionotropic glutamate receptors in the central nervous system. The chem. synthesis of DA and its derivatives requires considerable effort to establish a pyrrolidine ring containing three contiguous stereocenters. Recently, a biosynthetic cyclase for DA, DabC, was identified. This enzyme cyclizes the linear precursor of isodomoic acid A (IA) to IA, a bioactive DA analog. In this study, we developed a bioconversion system to obtain DA analogs from linear substrates prepared by simple chem. synthesis using DabC expressed in Escherichia coli, in vivo. Three IA analogs with various substitutions at the C7′-geranyl terminus were prepared using this system: two minor natural analogs, 7′-methyl-IA (5) and 7′-hydroxy-IA (6), and one new unnatural analog, 7′-amide-IA (7). In addition, the toxicity of these DA analogs in mice was examined by intracerebroventricular injection. Most of the mice injected with 5 (3 nmol) and 6 (3 nmol) did not show any adverse symptoms, whereas the mice injected with 7 (3 nmol) showed typical symptoms induced by DA (1, 0.7 nmol) and IA (2, 3 nmol). These results suggest that the 7′-carbonyl group in the side chain of IA (2) is crucial for its toxicity. The docking studies of DA, IA (2), 5, 6, and 7 to GluK1 supported these results. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate).
(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate
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