This work describes the possibility to combine multicomponent chemistry and multienzymes cascade transformations in a unique reactive framework to yield highly functionalized 1,4-benzoxazines under favorable heterogeneous conditions. The synthetic scheme involved the generation in situ of electrophilic reactive quinone intermediates of tyrosol esters catalyzed by lipase M and tyrosinase followed by nucleophilic 1,6-Michael addition of selected α-amino acid methyl esters, and successive intramolecular lactonization and aromatization processes. The immobilization of the multienzymes cascade on electroactive lignin nanoparticles improved the sustainability and recyclability of the overall system.

Synthesis of benzoxazines by heterogeneous multicomponent biochemo ultienzymes cascade reaction / Tomaino, E., Capecchi, E., Ubertini, V., Piccinino, D., Bizzarri, B.M., Saladino, R.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 89:4(2024), pp. 2343-2350. [10.1021/acs.joc.3c02314]

Synthesis of benzoxazines by heterogeneous multicomponent biochemo ultienzymes cascade reaction

Saladino, Raffaele
2024

Abstract

This work describes the possibility to combine multicomponent chemistry and multienzymes cascade transformations in a unique reactive framework to yield highly functionalized 1,4-benzoxazines under favorable heterogeneous conditions. The synthetic scheme involved the generation in situ of electrophilic reactive quinone intermediates of tyrosol esters catalyzed by lipase M and tyrosinase followed by nucleophilic 1,6-Michael addition of selected α-amino acid methyl esters, and successive intramolecular lactonization and aromatization processes. The immobilization of the multienzymes cascade on electroactive lignin nanoparticles improved the sustainability and recyclability of the overall system.
2024
lignin nanoparticles; concanavalin-a; derivatives; oxidation; lipase; 1,4-benzoxazine; peptidomimetics; tyrosinase; chemistry; catalyzes
01 Pubblicazione su rivista::01a Articolo in rivista
Synthesis of benzoxazines by heterogeneous multicomponent biochemo ultienzymes cascade reaction / Tomaino, E., Capecchi, E., Ubertini, V., Piccinino, D., Bizzarri, B.M., Saladino, R.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 89:4(2024), pp. 2343-2350. [10.1021/acs.joc.3c02314]
File allegati a questo prodotto
File Dimensione Formato  
Tomaino_Synthesis_2024.pdf

solo gestori archivio

Tipologia: Versione editoriale (versione pubblicata con il layout dell'editore)
Licenza: Tutti i diritti riservati (All rights reserved)
Dimensione 2.24 MB
Formato Adobe PDF
2.24 MB Adobe PDF   Contatta l'autore

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1766469
Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 8
  • ???jsp.display-item.citation.isi??? 8
social impact