RT Journal Article
T1 Green Enzymatic Synthesis of Geranyl Butyrate: Process Optimization and Mechanistic Insights
A1 Simão Neto, Francisco
A1 Sousa Junior, Paulo Gonçalves de
A1 da Silva Filho, Carlos José Alves
A1 Pinheiro Coutinho, Lucas
A1 Melo, Rafael Leandro Fernandes
A1 Rocha Martín, Javier
A1 Rios, Maria Alexsandra de Sousa
A1 Sanders Lopes, Ada Amélia
A1 Monteiro, Norberto de K. V.
A1 de Mattos, Marcos Carlos
A1 Serafim, Leonardo Farias
A1 Sousa dos Santos, José Cleiton
AB Flavor esters are organic compounds widely used in the food industry to enhance the aroma and taste of products. However, most chemical processes for the production of these flavoring compounds use toxic organic solvents. Some organic solvents derived from petroleum can leave behind residual traces in food products, which may raise concerns about potential health risks and contamination. In this study, we employ Eversa Transform 2.0, a commercial lipase derived from the lipase from Thermomyces lanuginosus, to produce geranyl butyrate in aqueous media. The chemical process was optimized using the Taguchi method, and a conversion of 93% was obtained at the optimal reaction conditions of: 1:5 molar ratio (v/v), 15% biocatalyst load (w/w), at 50 °C, in 6 h. Classic (molecular dynamics) and quantum (density functional theory) simulations unveiled amino acid residues involved in the stabilization of the enzyme–substrate complex. Detailed QM/MM mechanistic studies identified the nucleophilic attack of the deacylation reaction as the rate-limiting step of the entire mechanism, which has a free energy barrier of 14.0 kcal/mol.
PB American Chemical Society
SN 2470-1343
YR 2024
FD 2024-04-01
LK https://hdl.handle.net/20.500.14352/118927
UL https://hdl.handle.net/20.500.14352/118927
LA eng
NO Simão Neto, F., Sousa Junior, P. G. d., da Silva Filho, C. J. A., Pinheiro Coutinho, L., Melo, R. L. F., Rocha-Martin, J., Rios, M. A. d. S., Sanders Lopes, A. A., Monteiro, N. d. K. V., de Mattos, M. C., Serafim, L. F., & Sousa dos Santos, J. C. (2023). Green Enzymatic Synthesis of Geranyl Butyrate: Process Optimization and Mechanistic Insights. ACS Omega. https://doi.org/10.1021/ACSOMEGA.3C08483
NO We gratefully acknowledge the following Brazilian Agencies for Scientific and Technological Development: Fundação Cearense de Apoio ao Desenvolvimento Científico e Tecnológico (FUNCAP) (PS1-0186-00216.01.00/21; UNI-0210-00537.01.00/23), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (311062/2019-9; 440891/2020-5; 307454/2022-3), and Coordenação de Aperfeiçoamento de Ensino Superior (CAPES) (finance code 001). The authors thank the Northeastern Center for Application and Use of NMR (CENAUREMN) for NMR spectroscopy.
NO Fundação Cearense de Apoio ao Desenvolvimento Cientif́ico e Tecnológico (Brazil)
NO Conselho Nacional de Desenvolvimento Científico e Tecnológico (Brazil)
NO CAPES (Brazil)
DS Docta Complutense
RD 17 abr 2025