Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of a catalytic amount of B(CF). The perbenzylated glucosyl α-imidate provides β-selective glycosides in 70-92% yields.
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http://dx.doi.org/10.1021/acs.joc.8b00215 | DOI Listing |
Nat Commun
December 2024
School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210, China.
The strain-release-driven reactions of bicyclo[1.1.0]butanes (BCBs) have received significant attention from chemists.
View Article and Find Full Text PDFBiotechnol Adv
December 2024
Department of Food Science and Biotechnology, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, Republic of Korea.
The selective oxyfunctionalization of unsaturated fatty acids is difficult in chemical reactions, whereas regio- and stereoselective oxyfunctionalization is often performed in biocatalytic synthesis. Fatty acid oxygenases, including hydratases, lipoxygenases, dioxygenases, diol synthases, cytochrome P450 monooxygenases, peroxygenases, and 12-hydroxylases, are used to convert C16 and C18 unsaturated fatty acids to diverse regio- and stereoselective mono-, di-, and trihydroxy fatty acids via selective oxyfunctionalization. The formed hydroxy fatty acids or hydroperoxy fatty acids are metabolized to industrially important oxygenated chemicals such as lactones, green leaf volatiles, and bioplastic monomers, including ω-hydroxy fatty acids, α,ω-dicarboxylic acids, and fatty alcohols, by biocatalysts.
View Article and Find Full Text PDFJ Nat Prod
December 2024
Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, China.
The first total syntheses of four isoflavone glucosides, tectoridin (), tectoridin A (), tectorigenin 7--β-d-glucopyranosyl-12--β-d-glucopyranoside (), and isotectroigenin 7--β-d-glucopyranoside (), have been accomplished. Key steps in our synthetic approach include a regioselective halogenation reaction, followed by methanolysis to introduce the -OCH group into isoflavone frameworks and a PTC-promoted stereoselective glycosidation to establish glycosidic bonds. The synthesized isoflavone glucosides (-) and their corresponding aglycones ( and ) were evaluated for anti-inflammatory activity against nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1 β (IL-1β) in lipopolysaccharide (LPS)-induced RAW264.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
East China Normal University, School of Chemistry and Molecular Engineering, 3663 N. Zhongshan Rd., 200062, Shanghai, CHINA.
We present a novel electrochemical dicarboxylation of epoxides with CO2, characterized by the cleavage of two C-O single bonds. Not only are vinyl epoxides viable, but cyclic carbonates also serve as effective substrates, facilitating the synthesis of E-configured adipic and octanedioic acids with high chemo-, regio-, and stereoselectivity. The synthetic practicality is further highlighted by the diverse functionalizations of the resulting multifunctional diacids.
View Article and Find Full Text PDFEnzyme Microb Technol
December 2024
College of Biomass Science and Engineering, Sichuan University, Chengdu 610065, China.
Calcidiol (25(OH)VD) and calcitriol (1α,25(OH)VD) are active vitamin D with high medicinal value, which can maintain calcium and phosphorus balance and treat vitamin D deficiency. Microbial synthesis is an important method to produce high-value-added compounds. It can produce active vitamin D through the hydroxylation reaction of P450, which can reduce the traditional chemical synthesis steps, and greatly improve the production efficiency and economic benefits.
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