10.1021/ol2024746
The research discusses the synthesis of the C1–C20 and C15–C27 segments of Aplyronine A, a potent cytotoxic macrolide isolated from the sea hare Aplysia kurodai. The study employs vinyl sulfone chemistry as a key strategy, utilizing oxidative cleavage of cyclic vinyl sulfones to prepare crucial fragments. The synthesis involves the union of key precursors through Horner-Wadsworth-Emmons and Julia-Kociensky olefination reactions. Reactants include cyclic vinyl sulfones, chiral building blocks, and various reagents for protection and deprotection steps, oxidations, and olefination. Analytical techniques used include spectroscopic methods (1H NMR, 13C NMR, HRMS), HPLC, and mass spectrometry to monitor the progress and purity of the synthesized compounds. The research also details the optimization of reaction conditions, such as pH and temperature, and the use of specific catalysts and reagents to achieve high yields and selectivity in the synthesis steps.
10.1002/anie.201308984
The research focuses on the development and systematic comparison of peptidic proteasome inhibitors, with a particular emphasis on the α-ketoamide electrophile as a promising reversible lead motif for therapeutic applications in oncological and immunological contexts. The study involves a series of in vitro, in vivo, and structural experiments to evaluate the implications of altered functionality and chemical reactivity of different electrophilic warheads on the inhibitory potential of the compounds. The researchers synthesized a range of inhibitors with varying electrophilic headgroups, including α-ketoaldehydes, α',β'-epoxyketones, boronic acids, and vinylsulfone, all based on the Z-Leu-Leu-Leu backbone. They performed IC50 measurements to assess the chymotrypsin-like activity of the proteasome, conducted crystallographic binding analysis to understand the binding profiles at the atomic level, and evaluated the cytotoxic effects in HeLa cell cultures. The experiments involved the use of various biochemical and structural methods, such as Grignard reactions, oxidation with 2-iodoxybenzoic acid (IBX), and synchrotron radiation for data recording. The analyses included IC50 measurements, Alamar Blue viability assays, and pulse chase experiments to study the kinetic behavior of the compounds. The results indicated that α-ketoamides, despite lacking a second strong electrophile, showed high binding affinities and selectivity for malignant tumor cells, suggesting their potential for expanded utility in chemo- and immunosuppressive therapies.
10.1016/S0040-4039(97)00175-5
The research focuses on the synthesis and reactions of alkynylselenonium salts with benzenesulfinic acid or its sodium salt. The purpose of the study was to investigate the reactions of these salts, which have been less explored compared to alkynyliodonium salts, with mild nucleophiles. The main conclusion was that reactions with sodium benzenesulfinate yielded (Z)-alkoxyvinylsulfones as the primary products, while reactions with benzenesulfinic acid resulted in (Z)-(β-phenylsulfonyl)vinylselenonium salts. The study also proposed an addition-elimination mechanism for the formation of vinylsulfones, which is currently under further investigation.
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