A method for the palladium-catalyzed arylation of α,β-unsaturated valerolactams is reported. This new protocol provides arylation products in yields up to 95% and is applicable to a wide array of aryl and heteroaryl bromides. The optimization, scope and limitations are described.
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http://dx.doi.org/10.1039/c6ob01126h | DOI Listing |
Medium-sized 5- and 6-membered ring lactams are molecules with remarkable stability, in contrast to smaller β-lactams. As monomers, they grant access to nylon-4 and nylon-5, which are alternative polyamides to widespread caprolactam-based nylon-6. Chemical hydrolysis of monocyclic γ- and δ-lactams to the corresponding amino acids requires harsh reaction conditions and up to now, no mild (enzymatic) protocol has been reported.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2024
Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Renmin Street 5625, Changchun, 130022, People's Republic of China.
Nylon, a widely-used high-performance thermoplastic, boasts exceptional durability and resistance to various solvents and weak acids, making it indispensable across diverse applications. However, its nonbiodegradable nature has led to alarming environmental pollution in land and oceans. Chemical recycling to monomers (CRM) stands as a crucial strategy for establishing a circular plastic economy, but the CRM of nylon remains largely unexplored.
View Article and Find Full Text PDFBioorg Med Chem Lett
January 2024
Department of Medicinal Chemistry and University of Florida, Gainesville, FL, 32610, USA. Electronic address:
Selective removal of senescent cells (SnCs) offers a promising therapeutic strategy to treat chronic and age-related diseases. Our prior investigations led to the discovery of piperlongumine (PL) and its derivatives as senolytic agents. In this study, our medicinal chemistry campaign on both the α,β-unsaturated δ-valerolactam ring and the phenyl ring of PL culminated in the identification of compound 24, which exhibited an impressive 50-fold enhancement in senolytic activity against senescent WI-38 fibroblasts compared to PL.
View Article and Find Full Text PDFMetab Eng
September 2023
Metabolic and Biomolecular Engineering National Research Laboratory and Systems Metabolic Engineering and Systems Healthcare Cross-Generation Collaborative Laboratory, Department of Chemical and Biomolecular Engineering (BK21 four), Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea; KAIST Institute for the BioCentury and KAIST Institute for Artificial Intelligence, KAIST, Daejeon, 34141, Republic of Korea; BioProcess Engineering Research Center and BioInformatics Research Center, KAIST, 34141, Daejeon, Republic of Korea. Electronic address:
Valerolactam (VL) is an important precursor chemical for nylon-5 and nylon 6,5. It has been produced by petroleum-based route involving harsh reaction conditions and generating toxic wastes. Here, we report the complete biosynthesis of VL by metabolically engineered Corynebacterium glutamicum overproducing L-lysine.
View Article and Find Full Text PDFNat Commun
April 2023
Metabolic and Biomolecular Engineering National Research Laboratory, Department of Chemical and Biomolecular Engineering (BK21 four), Institute for the BioCentury, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea.
Synthetic sRNAs allow knockdown of target genes at translational level, but have been restricted to a limited number of bacteria. Here, we report the development of a broad-host-range synthetic sRNA (BHR-sRNA) platform employing the RoxS scaffold and the Hfq chaperone from Bacillus subtilis. BHR-sRNA is tested in 16 bacterial species including commensal, probiotic, pathogenic, and industrial bacteria, with >50% of target gene knockdown achieved in 12 bacterial species.
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