Aerogel microspheres of chitosan, an abundant biopolymer obtained from marine crustaceans, have been successfully applied to catalyze the asymmetric aldol reaction in water, providing the products in high yields and with good stereoselectivity (up to 93% ee) and recyclability (up to 4 runs). Yields were favourably affected by additives such as DNP and stearic acid.
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http://dx.doi.org/10.1039/c0cc01502d | DOI Listing |
Adv Sci (Weinh)
January 2025
College of Pharmacy, Key Laboratory of Protection, Development and Utilization of Medicinal Resources in Liupanshan Area, Ministry of Education, Ningxia Medical University, Yinchuan, 750004, P.R. China.
Hispidin (1) is a polyphenolic compound with a wide range of pharmacological activities that is distributed in both plants and fungi. In addition to natural extraction, hispidin can be obtained by chemical or enzymatic synthesis. In this study, the identification and characterization of an undescribed enzyme, PheG, from Phellinus igniarius (P.
View Article and Find Full Text PDFMolecules
January 2025
Institute for Organic Synthesis and Photoreactivity of the Italian National Research Council, Area della Ricerca di Bologna, Via P. Gobetti, 101, 40129 Bologna, Italy.
The utilization of the homogeneous ()-2-pyrrolidine-tetrazole organocatalyst (Ley catalyst) in the self-condensation of ethyl pyruvate and cross-aldol reactions of ethyl pyruvate donor with non-enolizable pyruvate acceptors, namely the sterically hindered ethyl 3-methyl-2-oxobutyrate or the highly electrophilic methyl 3,3,3-trifluoropyruvate, is described as the key enantioselective step toward the synthesis of the corresponding biologically relevant isotetronic acids featuring a quaternary carbon functionalized with ester and alkyl groups. The transition from homogeneous to heterogeneous flow conditions is also investigated, detailing the fabrication and operation of packed-bed reactors filled with a silica-supported version of the pyrrolidine-tetrazole catalyst (SBA-15 as the matrix).
View Article and Find Full Text PDFLife (Basel)
December 2024
Department of Chemistry & Biochemistry, University of San Diego, San Diego, CA 92110, USA.
Using computational methods, we examine if the presence of HS can tame the unruly formose reaction by generating a free energy map of the reaction thermodynamics and kinetics of sulfur analogs within the core cycle. With mercaptoaldehyde as the linchpin C species, and feeding the cycle with CHO, selected aldol additions and enolizations are kinetically more favorable. Thione formation is thermodynamically less favored compared to aldehydes and ketones, but all these species can be connected by enolization reactions.
View Article and Find Full Text PDFOrg Lett
January 2025
Key Laboratory of Environment-Friendly Composite Materials of the State Ethnic Affairs Commission, Key Laboratory for Utility of Environment-Friendly Composite Materials and Biomass in University of Gansu Province, College of Chemical Engineering, Northwest Minzu University, Lanzhou 730030, P. R. China.
An efficient phospha-aldol/Meyer-Schuster rearrangement cascade reaction between propargylic aldehydes and phosphine oxides has been developed in which various phosphoryl enones were obtained in moderate to excellent yields. A comprehensive series of mechanistic experiments, including the identification of key intermediates and the application of O isotope labeling, has confirmed that this cascade reaction proceeds through a phospha-aldol followed by Meyer-Schuster rearrangement cascade reaction.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India.
Aldolases, especially 2-deoxyribose-5-phosphate aldolase (DERA) enzymes, have been widely employed to access key chiral precursors for various active pharmaceutical ingredients (APIs). This has been enabled by expanding their substrate scope toward non-natural acceptors and donors via protein engineering. In this study, we endeavored to broaden the acceptor substrate scope of DERA from sp.
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