On-Resin Selenopeptide Catalysts: Synthesis and Applications of Enzyme-Mimetic Reactions and Cyclization of Unsaturated Carboxylic Acids

Molecules, Journal Year: 2025, Volume and Issue: 30(3), P. 480 - 480

Published: Jan. 22, 2025

Selenium reagents are useful for selenoenzyme-mimicking reactions, as well organic synthesis. However, the reaction waste containing selenium frequently smells unpleasant and exhibits serious toxicity. Herein, we have developed new-type on-resin reagents, H-UXX···-PAM (5) Ac-(X)U*XX···-PAM (6), where U U* represent selenocysteine (U) p-methoxybenzyl (PMB)-protected U, respectively, recyclable catalysts, in which U-containing peptide chains linked to polystyrene resin PAM. Synthesized selenopeptides 5a–g with a variable amino acid sequence were evaluated their glutathione peroxidase (GPx)-like activity using UV 1H NMR methods, between dithiothreitol (DTTred) H2O2 methanol. It was found that intramolecular interaction basic residue, such histidine (H) lysine (K), enhances through formation of an NH···Se hydrogen bond. On other hand, catalytic 6a–d oxidative cyclization β,γ-unsaturated acids (7) into α,β-unsaturated lactones (8). Although yield 8 significantly decreased after second- or third-round reaction, due detachment moiety from resin, results demonstrated reusability, substrate scope 6 catalyst. Since is natural acid, potential targets novel-type green redox catalysts.

Language: Английский

Recent Advances in Selenium‐Mediated Redox Functional Group Interconversions

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 22, 2024

Abstract The conversion of a functional group into another represents the core organic synthesis. Within arena interconversions, oxidative and reductive transformations occupy privileged position development new sustainable, selective, general methodologies continue to attract significant interest. Owing versatility their chemistry, selenium compounds offer opportunities achieve both oxidation reduction wide range groups. Additionally, possibility generate in situ active oxidant or reducing species from suitable inert precursors enables catalytic processes. In this review, recent advances selenium‐mediated with particular emphasis on cutting‐edge researches bringing about insights comprehension mechanistic aspects, will be discussed.

Language: Английский