Green Enzymatic Synthesis of Geranyl Butyrate: Process Optimization and Mechanistic Insights.

Autor:	Simão Neto F; Department of Chemical Engineering, Federal University of Ceara, Fortaleza, Ceará 60455-760, Brazil., Sousa Junior PG; Department of Organic and Inorganic Chemistry, Federal University of Ceara, Fortaleza, Ceará 60440-900, Brazil., da Silva Filho CJA; Department of Organic and Inorganic Chemistry, Federal University of Ceara, Fortaleza, Ceará 60440-900, Brazil., Pinheiro Coutinho L; Department of Analytical Chemistry and Physical Chemistry, Federal University of Ceara, Fortaleza, Ceará 60020-181, Brazil., Melo RLF; Department of Metallurgic Engineering, Federal University of Ceara, Fortaleza, Ceará 60440-554, Brazil., Rocha-Martin J; Department of Biochemistry and Molecular Biology, Faculty of Biological Sciences, Complutense University of Madrid, Madrid 28040, Spain., Rios MAS; Department of Mechanical Engineering, Federal University of Ceara, Fortaleza, Ceará 60455-760, Brazil., Sanders Lopes AA; Engineering and Sustainable Development Institute, University of International Integration of Afro-Brazilian Lusophony, Redenção, Ceará 62790-970, Brazil., Monteiro NKV; Department of Analytical Chemistry and Physical Chemistry, Federal University of Ceara, Fortaleza, Ceará 60020-181, Brazil., de Mattos MC; Department of Analytical Chemistry and Physical Chemistry, Federal University of Ceara, Fortaleza, Ceará 60020-181, Brazil., Serafim LF; Department of Chemistry, Georgia State University, Atlanta, Georgia 30302, United States., Sousa Dos Santos JC; Engineering and Sustainable Development Institute, University of International Integration of Afro-Brazilian Lusophony, Redenção, Ceará 62790-970, Brazil.
Jazyk:	angličtina
Zdroj:	ACS omega [ACS Omega] 2024 Apr 01; Vol. 9 (15), pp. 16992-17001. Date of Electronic Publication: 2024 Apr 01 (Print Publication: 2024).
DOI:	10.1021/acsomega.3c08483
Abstrakt:	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. Competing Interests: The authors declare no competing financial interest. (© 2024 The Authors. Published by American Chemical Society.)
Databáze:	MEDLINE
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