Reagent-induced asymmetric induction in addition reaction of reduced glutathione onto bis-Mannich chalcones

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dc.creatorValeze, Aline Bernardes
dc.creatorD´Oliveira, Giulio Demetrius Creazzo
dc.creatorSilezin, Aneta
dc.creatorKuzma, Mónika
dc.creatorMolnár, Szilárd
dc.creatorNoda Pérez, Caridad
dc.creatorPerjési, Pál
dc.date.accessioned2023-08-24T10:31:39Z
dc.date.available2023-08-24T10:31:39Z
dc.date.issued2018
dc.description.abstractThe stereochemistry of non-enzyme catalyzed nucleophilic addition of GSH to 4′-hydroxychalcone 1 and its bis-Mannich derivative 2 was investigated at different pH values (pH 3.2, 6.1, 7.4, and 8.0). The stereochemical outcome of the reactions was evaluated by HPLC-UV-Vis method. Under strongly acidic conditions (pH 3.2), an unexpected diastereoselective addition of GSH onto the bis-Mannich derivative 2 was observed. Such a selectivity could not be observed in the similar reaction of 2 with N-acetylcysteine. The observed stereoselectivity can be rationalized by ion-pair formation between the protonated Mannich nitrogens and the deprotonated GSH(glutamate)-carboxylate. To the best of our knowledge, this is the first example of reagent-induced asymmetric induction in Michael-type additions of thiols.pt_BR
dc.identifier.citationBERNARDES, Aline et al. Reagent-induced asymmetric induction in addition reaction of reduced glutathione onto bis-Mannich chalcones. Archiv der Pharmazie: Chemistry in Life Sciences, Weinheim, v. 351, n. 7, e1700386, 2018. DOI: 10.1002/ardp.201700386. Disponível em: https://onlinelibrary.wiley.com/doi/10.1002/ardp.201700386. Acesso em: 17 ago. 2023.pt_BR
dc.identifier.doi10.1002/ardp.201700386
dc.identifier.issn0365-6233
dc.identifier.issne- 1521-4184
dc.identifier.urihttps://onlinelibrary.wiley.com/doi/10.1002/ardp.201700386
dc.language.isoengpt_BR
dc.publisher.countryAlemanhapt_BR
dc.publisher.departmentInstituto de Química - IQ (RMG)pt_BR
dc.rightsAcesso Restritopt_BR
dc.subjectChalconespt_BR
dc.subjectGlutathionept_BR
dc.subjectMichael reactionpt_BR
dc.subjectReagent-controlled asymmetric additionpt_BR
dc.titleReagent-induced asymmetric induction in addition reaction of reduced glutathione onto bis-Mannich chalconespt_BR
dc.typeArtigopt_BR

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