Details
| Original language | English |
|---|---|
| Pages (from-to) | 5926–5936 |
| Number of pages | 11 |
| Journal | ACS Sustainable Chemistry and Engineering |
| Volume | 11 |
| Issue number | 15 |
| Early online date | 6 Apr 2023 |
| Publication status | Published - 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.
Keywords
- (trans)esterification, COSMO-RS, deep eutectic solvents, lactose esters, molecular dynamics simulation
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
- Environmental Science(all)
- Environmental Chemistry
- Chemical Engineering(all)
- General Chemical Engineering
- Energy(all)
- Renewable Energy, Sustainability and the Environment
Sustainable Development Goals
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: ACS Sustainable Chemistry and Engineering, Vol. 11, No. 15, 17.04.2023, p. 5926–5936.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
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.
AB - 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.
KW - (trans)esterification
KW - COSMO-RS
KW - deep eutectic solvents
KW - lactose esters
KW - molecular dynamics simulation
UR - http://www.scopus.com/inward/record.url?scp=85152209456&partnerID=8YFLogxK
U2 - 10.1021/acssuschemeng.2c07607
DO - 10.1021/acssuschemeng.2c07607
M3 - Article
AN - SCOPUS:85152209456
VL - 11
SP - 5926
EP - 5936
JO - ACS Sustainable Chemistry and Engineering
JF - ACS Sustainable Chemistry and Engineering
SN - 2168-0485
IS - 15
ER -