Deep Eutectic Solvents as Suitable Solvents for Lipase-Catalyzed Transesterification Reactions.
biocatalysis
deep eutectic solvent
glucose esters
lipase
transesterification
Journal
ChemSusChem
ISSN: 1864-564X
Titre abrégé: ChemSusChem
Pays: Germany
ID NLM: 101319536
Informations de publication
Date de publication:
20 Oct 2023
20 Oct 2023
Historique:
revised:
20
06
2023
received:
27
04
2023
medline:
26
10
2023
pubmed:
10
7
2023
entrez:
9
7
2023
Statut:
ppublish
Résumé
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).
Identifiants
pubmed: 37423894
doi: 10.1002/cssc.202300615
doi:
Substances chimiques
Solvents
0
vinyl laurate
0
Laurates
0
Lipase
EC 3.1.1.3
Deep Eutectic Solvents
0
Choline
N91BDP6H0X
Glucose
IY9XDZ35W2
Acetates
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300615Subventions
Organisme : Portuguese Foundation for Science and Technology (FCT)
ID : UIDB/04469/2020
Organisme : FCT
ID : SFRH/BD/147190/2019
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
X. S. Lin, K. H. Zhao, Q. L. Zhou, K. Q. Xie, P. J. Halling, Z. Yang, Bioresour. Bioprocess. 2016, 3(2), 1-7.
X. S. Lin, Q. Wen, Z. L. Huang, Y. Z. Cai, P. J. Halling, Z. Yang, Process Biochem. 2015, 50(11), 1852-1858.
T. Kobayashi, Biotechnol. Lett. 2011, 33, 1911-1919.
R. Hollenbach, B. Bindereif, U. S. Schaaf, K. Ochsenreither, C. Syldatk, Front. Bioeng. Biotechnol. 2020, 8, 1-10.
M. Pöhnlein, J. Ulrich, F. Kirschhöfer, M. Nusser, C. Muhle-Goll, B. Kannengiesser, G. Brenner-Weiß, B. Luy, A. Liese, C. Syldatk, R. Hausmann, Eur. J. Lipid Sci. Technol. 2015, 117(2), 161-166.
R. Hollenbach, K. Ochsenreither, C. Syldatk, Int. J. Mol. Sci. 2020, 21(12), 1-11.
S. Siebenhaller, C. Muhle-Goll, B. Luy, F. Kirschhöfer, G. Brenner-Weiss, E. Hiller, M. Günther, S. Rupp, S. Zibek, C. Syldatk, J. Mol. Catal. B 2016, 133, 281-287.
A. Mannu, M. Blangetti, S. Baldino, C. Prandi, Materials 2021, 14(10), 2494-2520.
M. A. Usman, O. K. Fagoroye, T. O. Ajayi, A. J. Kehinde, Appl. Petrochem. Res. 2020, 10, 125-137.
A. Yadav, S. Pandey, J. Chem. Eng. Data. 2014, 59(7), 2221-2229.
A. Yadav, S. Trivedi, R. Rai, S. Pandey, Fluid Phase Equilib. 2014, 367, 135-142.
M. Ishaq, M. A. Gilani, I. Arshad, M. R. Bilad, F. Ahmad, A. L. Khan, CCST 2021, 1, 1000019-1000028.
M. Shehata, A. Unlu, U. Sezerman, E. Timucin, J. Phys. Chem. B. 2020, 124(40), 8801-8810.
D. S. Freitas, V. Quesado, D. Rocha, J. Noro, M. Martins, A. Cavaco-Paulo, C. Silva, ChemSusChem 2023, 16(11), e202202374.
K.-H. Zhao, Y.-Z. Cai, X.-S. Lin, J. Xiong, P. J. Halling, Z. Yang, Molecules 2016, 21, 1294-1307.
M. K. AlOmar, M. Hayyan, M. A. Alsaadi, S. Akib, A. Hayyan, M. A. Hashim, J. Mol. Liq. 2016, 215, 98-103.
D. Yue, Y. Jia, Y. Yao, J. Sun, Y. Jing, Electrochim. Acta. 2012, 65, 30-36.
I. Delso, C. Lafuente, J. Muñoz-Embid, M. Artal, J. Mol. Liq. 2019, 290, 111236-111244.
J. Eed, Factors Affecting Enzyme Activity. 2012, ESSAI: Vol. 10, Article 19..
M. M. Shamel, M. Hasan, K. B. Ramachandran, Asia-Pac. J. Chem. Eng. 2008, 13, 599-604.
J. Noro, T. G. Castro, A. Cavaco-Paulo, C. Silva, Catal. Sci. Technol. 2020, 10, 5913-5924.
B. D. Ribeiro, L. C. Iff, M. A. Z. Coelho, I. M. Marrucho, Curr. Biochem. Eng. 2019, 5, 57-68.
A. P. Abbott, D. Boothby, G. Capper, D. L. Davies, R. K. Rasheed, J. Am. Chem. Soc. 2004, 126(29), 9142-9147.
A. Kovács, M. Yusupov, I. Cornet, P. Billen, E. C. Neyts, J. Mol. Liq. 2022, 366, 120180-120197.
Y. Yesiloglu, I. Kilic, JAOCS 2004, 81(3), 281-284.
S. Gogoi, M. G. Pathak, A. Dutta, N. N. Dutt, IJBB 2008, 45, 192-197.
H. Y. Lee, S. Kimura, T. Iwata, Biomacromolecules 2019, 20(2), 705-711.
H. S. Patil, D. D. Jadhav, A. Paul, F. A. Mulani, S. J. Karegaonkar, H. V. Thulasiram, Data Br. 2018, 18, 1134-1141.
H. Monhemi, M. R. Housaindokht, A. A. Moosavi-Movahedi, M. R. Bozorgmehr, Phys. Chem. Chem. Phys. 2014,16, 14882-14893.
D. S. Freitas, D. Rocha, T. G. Castro, J. Noro, V. I. B. Castro, M. A. Teixeira, R. L. Reis, A. Cavaco-Paulo, C. Silva, ACS Sustainable Chem. Eng. 2022, 10(24), 7974-7989.
D. Guimarães, J. Noro, A. Loureiro, A. Cavaco-Paulo, E. Nogueira, Colloids Surf. B. 2019, 179, 414-420.
J. Noro, T. G. Castro, F. Gonçalves, A. Ribeiro, A. Cavaco-Paulo, C. Silva, ChemCatChem 2019, 11(10), 2490-2499.