Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters: A Generalizable Strategy?

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Riccardo Semproli
  • Santiago Nahuel Chanquia
  • Jan Philipp Bittner
  • Simon Müller
  • Pablo Domínguez de María
  • Selin Kara
  • Daniela Ubiali

Organisationseinheiten

Externe Organisationen

  • Università degli Studi di Pavia
  • Aarhus University
  • Technische Universität Hamburg (TUHH)
  • Sustainable Momentum SL
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Details

OriginalspracheEnglisch
Seiten (von - bis)5926–5936
Seitenumfang11
FachzeitschriftACS Sustainable Chemistry and Engineering
Jahrgang11
Ausgabenummer15
Frühes Online-Datum6 Apr. 2023
PublikationsstatusVeröffentlicht - 17 Apr. 2023

Abstract

Sugar (fatty acid) esters are industrially relevant compounds, with a cumbersome production process due to the solubility issues of the substrates, which forces the use of environmentally unfriendly reaction media. Herein, deep eutectic solvents (DESs) are considered as a promising solution: several literature examples use glucose and different acyl donors to illustrate the efficient synthesis of sugar esters in classic DESs like choline chloride/urea (ChCl/U). However, this paper discloses that when sugars like lactose or other disaccharides are used, enzymes cannot efficiently perform (trans)esterifications in DESs, while the same reaction can proceed in mixtures like pyridine/tetrahydrofuran (Py/THF). This could be explained by computational solubility studies and molecular dynamics simulations of both reaction media, showing two effects: (i) on the one hand, large acyl donors (more than C10) display poor solubility in DESs and (ii) on the other hand, disaccharides interact with DES components. Thus, the DES affects the conformation of lactose (compared to the conformation observed in the Py/THF mixture), in such a way that the enzymatic reaction results impaired. Despite that classic DESs (e.g., ChCl/U) may not be useful for generalizing their use in saccharide ester syntheses, the achieved theoretical understanding of the reaction may enable the design of future DESs that can combine enzyme compatibility with eco-friendliness and efficiency in sugar chemistry.

Zitieren

Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters: A Generalizable Strategy? / Semproli, Riccardo; Chanquia, Santiago Nahuel; Bittner, Jan Philipp et al.
in: ACS Sustainable Chemistry and Engineering, Jahrgang 11, Nr. 15, 17.04.2023, S. 5926–5936.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Semproli, R, Chanquia, SN, Bittner, JP, Müller, S, Domínguez de María, P, Kara, S & Ubiali, D 2023, 'Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters: A Generalizable Strategy?', ACS Sustainable Chemistry and Engineering, Jg. 11, Nr. 15, S. 5926–5936. https://doi.org/10.1021/acssuschemeng.2c07607
Semproli, R., Chanquia, S. N., Bittner, J. P., Müller, S., Domínguez de María, P., Kara, S., & Ubiali, D. (2023). Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters: A Generalizable Strategy? ACS Sustainable Chemistry and Engineering, 11(15), 5926–5936. https://doi.org/10.1021/acssuschemeng.2c07607
Semproli R, Chanquia SN, Bittner JP, Müller S, Domínguez de María P, Kara S et al. Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters: A Generalizable Strategy? ACS Sustainable Chemistry and Engineering. 2023 Apr 17;11(15):5926–5936. Epub 2023 Apr 6. doi: 10.1021/acssuschemeng.2c07607
Semproli, Riccardo ; Chanquia, Santiago Nahuel ; Bittner, Jan Philipp et al. / Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters : A Generalizable Strategy?. in: ACS Sustainable Chemistry and Engineering. 2023 ; Jahrgang 11, Nr. 15. S. 5926–5936.
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title = "Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters: A Generalizable Strategy?",
abstract = "Sugar (fatty acid) esters are industrially relevant compounds, with a cumbersome production process due to the solubility issues of the substrates, which forces the use of environmentally unfriendly reaction media. Herein, deep eutectic solvents (DESs) are considered as a promising solution: several literature examples use glucose and different acyl donors to illustrate the efficient synthesis of sugar esters in classic DESs like choline chloride/urea (ChCl/U). However, this paper discloses that when sugars like lactose or other disaccharides are used, enzymes cannot efficiently perform (trans)esterifications in DESs, while the same reaction can proceed in mixtures like pyridine/tetrahydrofuran (Py/THF). This could be explained by computational solubility studies and molecular dynamics simulations of both reaction media, showing two effects: (i) on the one hand, large acyl donors (more than C10) display poor solubility in DESs and (ii) on the other hand, disaccharides interact with DES components. Thus, the DES affects the conformation of lactose (compared to the conformation observed in the Py/THF mixture), in such a way that the enzymatic reaction results impaired. Despite that classic DESs (e.g., ChCl/U) may not be useful for generalizing their use in saccharide ester syntheses, the achieved theoretical understanding of the reaction may enable the design of future DESs that can combine enzyme compatibility with eco-friendliness and efficiency in sugar chemistry.",
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note = "Funding Information: Cariplo Foundation (Italy) is gratefully acknowledged for the grant “Integrated platform for the sustainable production of bio-based surfactants from renewable resources (BioSurf)” to D.U. (ID 2020-1094, call: “Circular Economy for a sustainable future 2020”). S.K. thanks to Novo Nordisk Foundation, Light-BioFuels project, grant no. NNF19OC0057522, and Deutsche Forschungsgemeinschaft (DFG), grant no. KA 4399/3-2 and SM 82/25-2.",
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T1 - Deep Eutectic Solvents for the Enzymatic Synthesis of Sugar Esters

T2 - A Generalizable Strategy?

AU - Semproli, Riccardo

AU - Chanquia, Santiago Nahuel

AU - Bittner, Jan Philipp

AU - Müller, Simon

AU - Domínguez de María, Pablo

AU - Kara, Selin

AU - Ubiali, Daniela

N1 - Funding Information: Cariplo Foundation (Italy) is gratefully acknowledged for the grant “Integrated platform for the sustainable production of bio-based surfactants from renewable resources (BioSurf)” to D.U. (ID 2020-1094, call: “Circular Economy for a sustainable future 2020”). S.K. thanks to Novo Nordisk Foundation, Light-BioFuels project, grant no. NNF19OC0057522, and Deutsche Forschungsgemeinschaft (DFG), grant no. KA 4399/3-2 and SM 82/25-2.

PY - 2023/4/17

Y1 - 2023/4/17

N2 - Sugar (fatty acid) esters are industrially relevant compounds, with a cumbersome production process due to the solubility issues of the substrates, which forces the use of environmentally unfriendly reaction media. Herein, deep eutectic solvents (DESs) are considered as a promising solution: several literature examples use glucose and different acyl donors to illustrate the efficient synthesis of sugar esters in classic DESs like choline chloride/urea (ChCl/U). However, this paper discloses that when sugars like lactose or other disaccharides are used, enzymes cannot efficiently perform (trans)esterifications in DESs, while the same reaction can proceed in mixtures like pyridine/tetrahydrofuran (Py/THF). This could be explained by computational solubility studies and molecular dynamics simulations of both reaction media, showing two effects: (i) on the one hand, large acyl donors (more than C10) display poor solubility in DESs and (ii) on the other hand, disaccharides interact with DES components. Thus, the DES affects the conformation of lactose (compared to the conformation observed in the Py/THF mixture), in such a way that the enzymatic reaction results impaired. Despite that classic DESs (e.g., ChCl/U) may not be useful for generalizing their use in saccharide ester syntheses, the achieved theoretical understanding of the reaction may enable the design of future DESs that can combine enzyme compatibility with eco-friendliness and efficiency in sugar chemistry.

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