675-10-5Relevant articles and documents
Screening for enhanced triacetic acid lactone production by recombinant Escherichia coli expressing a designed triacetic acid lactone reporter
Tang, Shuang-Yan,Qian, Shuai,Akinterinwa, Olubolaji,Frei, Christopher S.,Gredell, Joseph A.,Cirino, Patrick C.
, p. 10099 - 10103 (2013)
Triacetic acid lactone (TAL) is a signature byproduct of polyketide synthases (PKSs) and a valuable synthetic precursor. We have developed an endogenous TAL reporter by engineering the Escherichia coli regulatory protein AraC to activate gene expression in response to TAL. The reporter enabled in vivo directed evolution of Gerbera hybrida 2-pyrone synthase activity in E. coli. Two rounds of mutagenesis and high-throughput screening yielded a variant conferring ~20-fold increased TAL production. The catalytic efficiency (kcat/Km) of the variant toward the substrate malonyl-CoA was improved 19-fold. This study broadens the utility of engineered AraC variants as customized molecular reporters. In addition, the TAL reporter can find applications in other basic PKS activity screens.
The first example of the [4+2] cycloaddition reaction of silylketenes with 1,3-dienes: A convenient preparation of 2-pyranones and isochromenes
Ito, Tatsuya,Aoyama, Toyohiko,Shioiri, Takayuki
, p. 6583 - 6586 (1993)
Silylketenes easily undergo the [4+2] cycloaddition reaction with electron-rich 1,3-dienes and o-quinodimethanes to give the corresponding 2-pyranones and isochromenes, respectively.
Synthesis, characterization and antimicrobial activity of some new azo dyes derived from 4-hydroxy-6-methyl-2H-pyran-2-one and its dihydro derivative
Ben Mohamed-Smati, Soumaya,Faraj, Fadhil Lafta,Becheker, Imène,Berredjem, Hadjira,Le Bideau, Franck,Hamdi, Maamar,Dumas, Fran?oise,Rachedi, Yahia
, (2021)
A series of new azo disperse dyes was synthesized by coupling 4-hydroxy-6-methyl-2H-pyran-2-one (triacetic acid lactone, TAL) or its hydrogenated derivative 4-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one (dihydro triacetic acid lactone, DHTAL) with diazonium salts derived from aniline, 4-bromoaniline, 4-nitroaniline, 4-methoxyaniline, 2,4-dimethoxyaniline and 2,5-dimethoxyaniline. Spectroscopic data of these dyes dissolved in five organic solvents were measured. The effects of solvent polarity, nucleophilic component and substituent nature on the visible absorption spectra of the dyes are also reported. The structures of all compounds were confirmed by FT-IR, electronic absorption in UV and visible regions, 1H, 13C and 2D NMR and high resolution mass spectroscopy (HRMS). In addition, in vitro antibacterial activity of the synthesized derivatives against Gram positive and Gram negative bacteria, both reference and clinical strains, was evaluated qualitatively and quantitatively by agar diffusion method.
Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation
Basu, Manas K.,Mukkanti, K.,Samala, Ramakrishna
, (2022/01/03)
Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields (58–80%). The utility of this methodology was exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.
The Generation of a Library of Bromodomain-Containing Protein Modulators Expedited by Continuous Flow Synthesis
Filipponi, Paolo,Baxendale, Ian R.
, p. 2000 - 2012 (2016/04/26)
A continuous flow process delivering key building blocks for a series of BCP modulator libraries is reported. A dynamically mixed flow reactor emerged as a pivotal technology in both synthesis and isolation phases enabling the processing of slurries and suspensions while maintaining high productivity and reliability. Accordingly, the synthesis of common intermediates in flow were employed to further build a pyridazone-based library (36 compounds) aimed at improving lead compound potency and selectivity while further enabling structure-activity relationship studies of a new BCP modulator family.