Deep Eutectic Solvents as Suitable Solvents for Lipase-Catalyzed Transesterification Reactions.

Autor: Noro J; Centre of Biological Engineering, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal.; LABBELS - Associate Laboratory, University of Minho, 4710-057, Braga, Guimarães, Portugal.; Solfarcos - Pharmaceutical and Cosmetic Solutions, 4710-053, Braga, Portugal., Cabo J; Centre of Biological Engineering, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal.; LABBELS - Associate Laboratory, University of Minho, 4710-057, Braga, Guimarães, Portugal., Freitas DS; Centre of Biological Engineering, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal.; LABBELS - Associate Laboratory, University of Minho, 4710-057, Braga, Guimarães, Portugal., Roque CS; Centre of Biological Engineering, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal.; LABBELS - Associate Laboratory, University of Minho, 4710-057, Braga, Guimarães, Portugal., de Castro M; Centre of Biological Engineering, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal.; LABBELS - Associate Laboratory, University of Minho, 4710-057, Braga, Guimarães, Portugal., Cavaco-Paulo A; Centre of Biological Engineering, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal.; LABBELS - Associate Laboratory, University of Minho, 4710-057, Braga, Guimarães, Portugal.; Solfarcos - Pharmaceutical and Cosmetic Solutions, 4710-053, Braga, Portugal., Silva C; Centre of Biological Engineering, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal.; LABBELS - Associate Laboratory, University of Minho, 4710-057, Braga, Guimarães, Portugal.
Jazyk: angličtina
Zdroj: ChemSusChem [ChemSusChem] 2023 Oct 20; Vol. 16 (20), pp. e202300615. Date of Electronic Publication: 2023 Aug 09.
DOI: 10.1002/cssc.202300615
Abstrakt: In this work, three deep eutectic mixtures (DES 1: choline chloride/urea; DES 2: choline chloride/glycerol; and DES 3: tetrabutylammonium bromide/imidazole) were investigated as mediums for the synthesis of glucose laurate and glucose acetate. Aiming to achieve a greener and more sustainable approach, the synthesis reactions were catalyzed by lipases from Aspergillus oryzae (LAO), Candida rugosa (LCR), and porcine pancreas (LPP). The hydrolytic activity of lipases against p-nitrophenyl hexanoate revealed no evidence of enzyme inactivation when DES were used as medium. Regarding the transesterification reactions, combining LAO or LCR with DES 3 resulted in the efficient production of glucose laurate (from glucose and vinyl laurate) (conversion >60 %). The best result for LPP was observed in DES 2, with 98 % of product production after 24 hours of reaction. When replacing vinyl laurate by a smaller hydrophilic substrate, vinyl acetate, a distinct behavior was observed. LCR and LPP performed better in DES 1, yielding more than 80 % of glucose acetate after 48 hours of reaction. The catalytic activity of LAO was less pronounced, reaching only nearly 40 % of product in DES 3. The results highlight the potential of combining biocatalysis with greener and environmentally-safer solvents, for the synthesis of differentiated chain-length sugar fatty acid esters (SFAE).
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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