The green synthesis of the flavor esters, n-propyl acetate, isobutyl acetate and isoamyl acetate had the advantages over the chemical synthesis. The esterase from Candida parapsilosis could transform n-propanol, isobutanol and isoamyl alcohol into n-propyl acetate, isobutyl acetate and isoamyl acetate, respectively. The esterase was expressed in Saccharomyces cerevisiae. At 30 °C for 1 d, the concentration of n-propyl acetate, isobutyl acetate and isoamyl acetate synthesized by the esterase expressed in Saccharomyces cerevisiae was 24.6 mg/100 mL, 8.3 mg/100 mL, 5.6 mg/100 mL, respectively. Expression of the esterase has a practical significance for flavor ester synthesis by green biochemical process.
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Sun JC, Yu B, Curran P, Liu SQ (2012) Lipase-catalysed transesterification of coconut oil with fusel alcohols in a solvent-free system. Food Chem 134:89–94. https://doi.org/10.1016/j.foodchem.2012.02.070
Krishna SH, Divakar S, Prapulla SG, Karanth NG (2001) Enzymatic synthesis of isoamyl acetate using immobilized lipase from Rhizomucor miehei. J Biotechnol 87:193–201. https://doi.org/10.1016/S0168-1656(00)00432-6
Langrand G, Rondot N, Triantaphylides C, Baratti J (1990) Short chain flavour esters synthesis by microbial lipases. Biotechnol Lett 12:581–586. https://doi.org/10.1007/bf01030756
Romero MD, Calvo L, Alba C, Habulin M, Primozic M, Knez Ž (2005) Enzymatic synthesis of isoamyl acetate with immobilized Candida antarctica lipase in supercritical carbon dioxide. J Supercrit Fluids 33:77–84. https://doi.org/10.1016/s0896-8446(04)00114-7
Mhetras N, Patil S, Gokhale D (2010) Lipase of Aspergillus niger NCIM 1207: a potential biocatalyst for synthesis of isoamyl acetate. Indian J Microbiol 50:432–437. https://doi.org/10.1007/s12088-011-0087-4
Patidar P, Mahajani SM (2012) Esterification of fusel oil using reactive distillation—part I: reaction kinetics. Chem Eng J 207–208:377–387. https://doi.org/10.1016/j.cej.2012.06.139
Kucuk Z, Ceylan K (1998) Potential utilization of fusel oil: a kinetic approach for production of fusel oil esters through chemical reaction. Turk J Chem 22:289–300. https://doi.org/10.1023/A:1019138718283
Surburg H, Panten J (2016) Common fragrance and flavor materials: preparation, properties and uses, 6th edn. John Wiley, New York. https://doi.org/10.1002/9783527693153.ch2
Akacha NB, Gargouri M (2015) Microbial and enzymatic technologies used for the production of natural aroma compounds: synthesis, recovery modeling, and bioprocesses. Food Bioprod Process 94:675–706. https://doi.org/10.1016/j.fbp.2014.09.011
Stergiou PY, Foukis A, Filippou M, Koukouritaki M, Parapouli M, Theodorou LG, Hatziloukas E, Afendra AM, Pandey A, Papamichael E (2013) Advances in lipase-catalyzed esterification reactions. Biotechnol Adv 31:1846–1859. https://doi.org/10.1016/j.biotechadv.2013.08.006
Rajendran A, Palanisamy A, Thangavelu V (2009) Lipase catalyzed ester synthesis for food processing industries. Braz Arch Biol Technol 52:207–219. https://doi.org/10.1590/S1516-89132009000100026
Choi J, Han S, Kim H (2015) Industrial applications of enzyme biocatalysis: current status and future aspects. Biotechnol Adv 33:1443–1454. https://doi.org/10.1016/j.biotechadv.2015.02.014
Kumar MBA, Gao Y, Shen W, He LZ (2015) Valorisation of protein waste: an enzymatic approach to make commodity chemicals. Front Chem Sci Eng 9:295–307. https://doi.org/10.1007/s11705-015-1532-4
Chen KQ, Cheng DG, Peng C, Wang D, Zhang JT (2018) Green catalytic engineering: a powerful tool for sustainable development in chemical industry. Front Chem Sci Eng 12:835–837. https://doi.org/10.1007/s11705-018-1756-1
Sebastián T, Baigori MD, Swathy SL, Pandey A, Castro GR (2009) Enzymatic synthesis of banana flavour (isoamyl acetate) by Bacillus licheniformis S-86 esterase. Food Res Int 42:454–460. https://doi.org/10.1016/j.foodres.2008.12.005
Shakiba MH, Ali MS, Rahman RN (2016) Cloning, expression and characterization of a novel cold adapted GDSL family esterase from Photobacterium sp. strain J15. Extremophiles 20:44–55. https://doi.org/10.1007/s00792-015-0796-4
Contesini FJ, Lopes DB, Macedo GA, Nascimento MG, Carvalho PO (2010) Aspergillus sp lipase: potential biocatalyst for industrial use. J Mol Catal B Enzym 67:163–171. https://doi.org/10.1016/j.molcatb.2010.07.021
Mendes AA, Oliveira PC, Castro HF (2012) Properties and biotechnological applications of porcine pancreatic lipase. J Mol Catal B Enzym 78:119–134. https://doi.org/10.1016/j.molcatb.2012.03.004
Ranjan R, Yadav M, Suneja G, Harma R (2018) Discovery of a diverse set of esterases from hot spring microbial mat and sea sediment metagenomes. Int J Biol Macromol 119:572–581. https://doi.org/10.1016/j.ijbiomac.2018.07.170
Kumar S, Stecher G, Tamura K (2018) MEGA7: molecular evolutionary genetics analysis version 7.0 for bigger datasets. Mol Biol Evolut 33:1870–1874. https://doi.org/10.1093/molbev/msw054
Saitou N, Nei M (1987) The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol Biol Evol 4:406–425. https://doi.org/10.1093/oxfordjournals.molbev.a040454
Grosch JH, Loderer C, Jestel T, Marion AS, Antje CS (2015) Carbonyl reductase of Candida parapsilosis-stability analysis and stabilization strategy. J Mol Catal B Enzym 112:45–53. https://doi.org/10.1016/j.molcatb.2014.12.001
Jiří D, Jiří B, Olga HH, Irena S, Pavlína Ř (2009) The crystal structure of the secreted aspartic protease 1 from Candida parapsilosis in complex with pepstatin A. J Struct Biol 167:145–152. https://doi.org/10.1016/j.jsb.2009.04.004
Subileau M, Jan A-H, Nozac’h H, Pérez-Gordo M, Perrier V, Dubreucq E (1854) The 3D model of the lipase/acyltransferase from Candida parapsilosis, a tool for the elucidation of structural determinants in CAL-A lipase superfamily. Biochem Biophys Acta 10:1400–1411. https://doi.org/10.1016/j.bbapap.2015.06.012
De Waele S, Vandenberghe I, Laukens B, Planckaert S, Verweire S, Van Bogaert INA, Soetaert W, Devreese B, Ciesielska K (2018) Optimized expression of the Starmerella bombicola lactone esterase in Pichia pastoris through temperature adaptation, codon-optimization and co-expression with HAC1. Protein Expr Purif. https://doi.org/10.1016/j.pep.2017.10.016
Zeng Y, Yin X, Wu MC, Yu T, Feng F, Zhu TD, Pang QF (2014) Expression of a novel feruloyl esterase from Aspergillus oryzae in Pichia pastoris with esterification activity. J Mol Catal B Enzym 110:140–146. https://doi.org/10.1016/j.molcatb.2014.10.002
Bond CM, Tang Y (2019) Engineering Saccharomyces cerevisiae for production of simvastatin. Metab Eng 51:1–8. https://doi.org/10.1016/j.ymben.2018.09.005
Iimura Y, Sonoki T, Habe H (2018) Heterologous expression of Trametes versicolor laccase in Saccharomyces cerevisiae. Protein Expr Purif 141:39–43. https://doi.org/10.1016/j.pep.2017.09.004
Aldridge WN (1993) The esterases: perspectives and problems. Chem Biol Interact 87:5–13. https://doi.org/10.1016/0009-2797(93)90019-U
Bornscheuer UT (2002) Microbial carboxyl esterases: classification, properties and application in biocatalysis. FEMS Microbiol Rev 26:73–81. https://doi.org/10.1111/j.1574-6976.2002.tb00599.x
Romano D, Bonomi F, Mattos MC, Fonseca TS, Oliveira MCF, Molinari F (2015) Esterases as stereoselective biocatalysts. Biotechnol Adv 33:547–565. https://doi.org/10.1016/j.biotechadv.2015.01.006
Henke E, Bornscheuer UT, Schmid RD, Pleiss J (2003) A molecular mechanism of enantiorecognition of tertiary alcohols by carboxylesterases. ChemBioChem 4:485–493. https://doi.org/10.1002/cbic.200200518
This work was supported by the Foundation of Hubei Provincial Department of Education (B2018040) and Research Fund for the Doctoral Program of Hubei University of Technology (No. BSQD14018).
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Xue, D., Yao, D., You, X. et al. Green Synthesis of the Flavor Esters with a Marine Candida parapsilosis Esterase Expressed in Saccharomyces cerevisiae. Indian J Microbiol (2020). https://doi.org/10.1007/s12088-020-00856-9
- Flavor ester
- Candida parapsilosis
- Saccharomyces cerevisiae