{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,25]],"date-time":"2026-06-25T12:18:51Z","timestamp":1782389931320,"version":"3.54.5"},"reference-count":36,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2022,8,30]],"date-time":"2022-08-30T00:00:00Z","timestamp":1661817600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2022,8,30]],"date-time":"2022-08-30T00:00:00Z","timestamp":1661817600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100004442","name":"Narodowym Centrum Nauki","doi-asserted-by":"publisher","award":["2019\/03\/X\/NZ9\/01684"],"award-info":[{"award-number":["2019\/03\/X\/NZ9\/01684"]}],"id":[{"id":"10.13039\/501100004442","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Sci Rep"],"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This work presents the chemo-enzymatic Baeyer\u2013Villiger oxidation of \u03b1-benzylcyclopentanones in ester solvents as well as deep eutectic solvents (DES). In the first part of the work the effect of selected reaction conditions on the reaction rate was determined. The oxidation process was most effective in ethyl acetate at 55\u00a0\u00b0C, with the use of lipase B from <jats:italic>Candida antarctica<\/jats:italic> immobilized on acrylic resin and UHP as oxidant. Ultimately, these preliminary studies prompted the development of an effective method for the implementation of lipase-mediated Baeyer\u2013Villiger oxidation of benzylcyclopentanones in DES. The highest conversion was indicated when the oxidizing agent was a component of DESs (minimal DESs). The fastest conversion of ketones to lactones was observed in a mixture of choline chloride with urea hydrogen peroxide. In this case, after 3\u00a0days, the conversion of the ketones to lactones products exceeded 92% for all substrates. As a result, two new lactones were obtained and fully characterized by spectroscopic data.<\/jats:p>","DOI":"10.1038\/s41598-022-18913-2","type":"journal-article","created":{"date-parts":[[2022,8,30]],"date-time":"2022-08-30T23:07:39Z","timestamp":1661900859000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Lipase-mediated Baeyer\u2013Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents"],"prefix":"10.1038","volume":"12","author":[{"given":"Marcelina","family":"Mazur","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomasz","family":"Janeczko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Witold","family":"G\u0142adkowski","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2022,8,30]]},"reference":[{"key":"18913_CR1","doi-asserted-by":"publisher","first-page":"363","DOI":"10.1016\/j.jscs.2016.04.004","volume":"22","author":"K Wi\u0144ska","year":"2018","unstructured":"Wi\u0144ska, K. et al. Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically. J. Saudi Chem. Soc. 22, 363\u2013371 (2018).","journal-title":"J. Saudi Chem. Soc."},{"key":"18913_CR2","doi-asserted-by":"publisher","first-page":"1032","DOI":"10.1021\/np800127b","volume":"71","author":"AM Pomini","year":"2008","unstructured":"Pomini, A. M. & Marsaioli, A. J. Absolute configuration and antimicrobial activity of acylhomoserine lactones. J. Nat. Prod. 71, 1032\u20131036 (2008).","journal-title":"J. Nat. Prod."},{"key":"18913_CR3","doi-asserted-by":"publisher","first-page":"489","DOI":"10.1002\/ps.4012","volume":"72","author":"M Mazur","year":"2016","unstructured":"Mazur, M. et al. Lactones 46: Synthesis, antifeedant and antibacterial activity of \u03b3-lactones with a p-methoxyphenyl substituent. Pest Manag. Sci. 72, 489\u2013496 (2016).","journal-title":"Pest Manag. Sci."},{"key":"18913_CR4","doi-asserted-by":"publisher","first-page":"286","DOI":"10.1002\/ps.3557","volume":"70","author":"M Mazur","year":"2014","unstructured":"Mazur, M. et al. Lactones 43: New biologically active lactones: \u03b2-cyclocitral derivatives. Pest Manag. Sci. 70, 286\u2013294 (2014).","journal-title":"Pest Manag. Sci."},{"key":"18913_CR5","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1016\/j.phytochem.2017.01.020","volume":"137","author":"ZN Wu","year":"2017","unstructured":"Wu, Z. N. et al. Sesquiterpene lactones from Elephantopus mollis and their anti-inflammatory activities. Phytochemistry 137, 81\u201386 (2017).","journal-title":"Phytochemistry"},{"key":"18913_CR6","doi-asserted-by":"publisher","first-page":"111","DOI":"10.1016\/j.bjp.2015.01.005","volume":"25","author":"AE Abe","year":"2015","unstructured":"Abe, A. E. et al. Anti-inflammatory sesquiterpene lactones from tithonia diversifolia trigger different effects on human neutrophils. Rev. Bras. Farmacogn. 25, 111\u2013116 (2015).","journal-title":"Rev. Bras. Farmacogn."},{"key":"18913_CR7","first-page":"543","volume":"7","author":"A Kamizela","year":"2018","unstructured":"Kamizela, A. et al. Synthesis, characterization, cytotoxicity, and antibacterial properties of trans-\u03b3-halo-\u03b4-lactones. Chem. Open 7, 543\u2013550 (2018).","journal-title":"Chem. Open"},{"key":"18913_CR8","doi-asserted-by":"publisher","first-page":"1218","DOI":"10.1111\/vco.12257","volume":"15","author":"A Pawlak","year":"2017","unstructured":"Pawlak, A. et al. A novel canine B-cell leukaemia cell line: Establishment, characterisation and sensitivity to chemotherapeutics. Vet. Comp. Oncol. 15, 1218\u20131231 (2017).","journal-title":"Vet. Comp. Oncol."},{"key":"18913_CR9","doi-asserted-by":"publisher","first-page":"1171","DOI":"10.1016\/j.bmcl.2018.03.006","volume":"28","author":"A Pawlak","year":"2018","unstructured":"Pawlak, A. et al. Enantiomeric trans \u03b2-aryl-\u03b4-iodo-\u03b3-lactones derived from 2,5-dimethylbenzaldehyde induce apoptosis in canine lymphoma cell lines by downregulation of anti-apoptotic Bcl-2 family members Bcl-xL and Bcl-2. Bioorg. Med. Chem. Lett. 28, 1171\u20131177 (2018).","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"18913_CR10","doi-asserted-by":"publisher","first-page":"6585","DOI":"10.1007\/s00253-016-7670-x","volume":"100","author":"M Bu\u010dko","year":"2016","unstructured":"Bu\u010dko, M. et al. Baeyer-Villiger oxidations: Biotechnological approach. Appl. Microbiol. Biotechnol. 100, 6585\u20136599 (2016).","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"18913_CR11","doi-asserted-by":"publisher","first-page":"340","DOI":"10.1016\/j.phytol.2012.02.015","volume":"5","author":"R Gni\u0142ka","year":"2012","unstructured":"Gni\u0142ka, R., Szumny, A., Bia\u0142o\u0144ska, A. & Wawrze\u0144czyk, C. Lactones 39: 1 chemical and microbial synthesis of lactones from (-)-\u03b1- and (+)-\u03b2-thujone. Phytochem. Lett. 5, 340\u2013345 (2012).","journal-title":"Phytochem. Lett."},{"key":"18913_CR12","doi-asserted-by":"publisher","first-page":"37","DOI":"10.1016\/j.catcom.2016.03.021","volume":"81","author":"A Drozdz","year":"2016","unstructured":"Drozdz, A., Hanefeld, U., Szyma\u0144ska, K., Jarz\u0229bski, A. & Chrobok, A. A robust chemo-enzymatic lactone synthesis using acyltransferase from Mycobacterium smegmatis. Catal. Commun. 81, 37\u201340 (2016).","journal-title":"Catal. Commun."},{"key":"18913_CR13","doi-asserted-by":"publisher","first-page":"459","DOI":"10.1039\/B618175A","volume":"9","author":"MY R\u00edos","year":"2007","unstructured":"R\u00edos, M. Y., Salazar, E. & Olivo, H. F. Baeyer\u2013Villiger oxidation of substituted cyclohexanones via lipase-mediated perhydrolysis utilizing urea\u2013hydrogen peroxide in ethyl acetate. Green Chem. 9, 459\u2013546 (2007).","journal-title":"Green Chem."},{"key":"18913_CR14","doi-asserted-by":"publisher","first-page":"1230","DOI":"10.1039\/C5CC08519E","volume":"52","author":"A Drozdz","year":"2016","unstructured":"Drozdz, A. & Chrobok, A. Chemo-enzymatic Baeyer\u2013Villiger oxidation of 4-methylcyclohexanone via kinetic resolution of racemic carboxylic acids: Direct access to enantioenriched lactone. Chem. Commun. 52, 1230\u20131233 (2016).","journal-title":"Chem. Commun."},{"key":"18913_CR15","doi-asserted-by":"publisher","first-page":"163","DOI":"10.1016\/j.apcata.2013.07.009","volume":"467","author":"A Drozdz","year":"2013","unstructured":"Drozdz, A. et al. The chemo-enzymatic Baeyer\u2013Villiger oxidation of cyclic ketones with an efficient silica-supported lipase as a biocatalyst. Appl. Catal. A Gen. 467, 163\u2013170 (2013).","journal-title":"Appl. Catal. A Gen."},{"key":"18913_CR16","doi-asserted-by":"publisher","first-page":"2576","DOI":"10.1039\/C7GC01127J","volume":"19","author":"S Ranganathan","year":"2017","unstructured":"Ranganathan, S., Zeitlhofer, S. & Sieber, V. Development of a lipase-mediated epoxidation process for monoterpenes in choline chloride-based deep eutectic solvents. Green Chem. 19, 2576\u20132586 (2017).","journal-title":"Green Chem."},{"key":"18913_CR17","doi-asserted-by":"publisher","first-page":"943","DOI":"10.1016\/j.tibtech.2019.03.007","volume":"37","author":"M P\u00e4tzold","year":"2019","unstructured":"P\u00e4tzold, M. et al. Deep eutectic solvents as efficient solvents in biocatalysis. Trends Biotechnol. 37, 943\u2013959 (2019).","journal-title":"Trends Biotechnol."},{"key":"18913_CR18","doi-asserted-by":"publisher","first-page":"27","DOI":"10.1016\/j.cogsc.2019.09.004","volume":"21","author":"FM Perna","year":"2020","unstructured":"Perna, F. M., Vitale, P. & Capriati, V. Deep eutectic solvents and their applications as green solvents. Curr. Opin. Green Sustain. Chem. 21, 27\u201333 (2020).","journal-title":"Curr. Opin. Green Sustain. Chem."},{"key":"18913_CR19","doi-asserted-by":"publisher","first-page":"1063","DOI":"10.1021\/sc500096j","volume":"2","author":"A Paiva","year":"2014","unstructured":"Paiva, A. et al. Natural deep eutectic solvents: Solvents for the 21st century. ACS Sustain. Chem. Eng. 2, 1063\u20131071 (2014).","journal-title":"ACS Sustain. Chem. Eng."},{"key":"18913_CR20","doi-asserted-by":"publisher","first-page":"8596","DOI":"10.1039\/D1CS00404B","volume":"50","author":"D Yu","year":"2021","unstructured":"Yu, D., Xue, Z. & Mu, T. Eutectics: Formation, properties, and applications. Chem. Soc. Rev. 50, 8596\u20138638 (2021).","journal-title":"Chem. Soc. Rev."},{"key":"18913_CR21","doi-asserted-by":"publisher","DOI":"10.1016\/j.seppur.2020.117196","volume":"250","author":"A Grudniewska","year":"2020","unstructured":"Grudniewska, A. & Pop\u0142o\u0144ski, J. Simple and green method for the extraction of xanthohumol from spent hops using deep eutectic solvents. Sep. Purif. Technol. 250, 117196 (2020).","journal-title":"Sep. Purif. Technol."},{"key":"18913_CR22","doi-asserted-by":"publisher","first-page":"15791","DOI":"10.1021\/acssuschemeng.8b04359","volume":"6","author":"A Grudniewska","year":"2018","unstructured":"Grudniewska, A. et al. Enhanced protein extraction from oilseed cakes using glycerol-choline chloride deep eutectic solvents: A biorefinery approach. ACS Sustain. Chem. Eng. 6, 15791\u201315800 (2018).","journal-title":"ACS Sustain. Chem. Eng."},{"key":"18913_CR23","doi-asserted-by":"publisher","first-page":"139","DOI":"10.1016\/j.progpolymsci.2017.09.005","volume":"78","author":"JD Mota-Morales","year":"2018","unstructured":"Mota-Morales, J. D. et al. Free-radical polymerizations of and in deep eutectic solvents: Green synthesis of functional materials. Prog. Polym. Sci. 78, 139\u2013153 (2018).","journal-title":"Prog. Polym. Sci."},{"key":"18913_CR24","doi-asserted-by":"publisher","first-page":"582","DOI":"10.1039\/D0RE00458H","volume":"6","author":"G Di Carmine","year":"2021","unstructured":"Di Carmine, G., Abbott, A. P. & D\u2019Agostino, C. Deep eutectic solvents: Alternative reaction media for organic oxidation reactions. React. Chem. Eng. 6, 582\u2013598 (2021).","journal-title":"React. Chem. Eng."},{"key":"18913_CR25","doi-asserted-by":"publisher","first-page":"1788","DOI":"10.1016\/j.procbio.2015.07.015","volume":"50","author":"M CvjetkoBubalo","year":"2015","unstructured":"CvjetkoBubalo, M., Mazur, M., Rado\u0161evi\u0107, K. & Radoj\u010di\u0107Redovnikovi\u0107, I. Baker\u2019s yeast-mediated asymmetric reduction of ethyl 3-oxobutanoate in deep eutectic solvents. Process Biochem. 50, 1788\u20131792 (2015).","journal-title":"Process Biochem."},{"key":"18913_CR26","doi-asserted-by":"publisher","first-page":"69","DOI":"10.1016\/j.procbio.2020.03.020","volume":"93","author":"D Pavokovi\u0107","year":"2020","unstructured":"Pavokovi\u0107, D., Ko\u0161pi\u0107, K., Pani\u0107, M., Radoj\u010di\u0107Redovnikovi\u0107, I. & CvjetkoBubalo, M. Natural deep eutectic solvents are viable solvents for plant cell culture-assisted stereoselective biocatalysis. Process Biochem. 93, 69\u201376 (2020).","journal-title":"Process Biochem."},{"key":"18913_CR27","doi-asserted-by":"publisher","first-page":"253","DOI":"10.1007\/s10529-018-2631-3","volume":"41","author":"M Pani\u0107","year":"2019","unstructured":"Pani\u0107, M., Dela\u010d, D., Roje, M., Radoj\u010di\u0107Redovnikovi\u0107, I. & CvjetkoBubalo, M. Green asymmetric reduction of acetophenone derivatives: Saccharomyces cerevisiae and aqueous natural deep eutectic solvent. Biotechnol. Lett. 41, 253\u2013262 (2019).","journal-title":"Biotechnol. Lett."},{"key":"18913_CR28","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.procbio.2020.12.001","volume":"102","author":"M Pani\u0107","year":"2021","unstructured":"Pani\u0107, M. et al. Development of environmentally friendly lipase-catalysed kinetic resolution of (R, S)-1-phenylethyl acetate using aqueous natural deep eutectic solvents. Process Biochem. 102, 1\u20139 (2021).","journal-title":"Process Biochem."},{"key":"18913_CR29","doi-asserted-by":"publisher","first-page":"129","DOI":"10.1016\/j.bej.2016.10.003","volume":"117","author":"I Juneidi","year":"2017","unstructured":"Juneidi, I., Hayyan, M., Hashim, M. A. & Hayyan, A. Pure and aqueous deep eutectic solvents for a lipase-catalysed hydrolysis reaction. Biochem. Eng. J. 117, 129\u2013138 (2017).","journal-title":"Biochem. Eng. J."},{"key":"18913_CR30","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1038\/s41598-016-0028-x","volume":"7","author":"XP Wang","year":"2017","unstructured":"Wang, X. P. et al. Engineering a lipase B from Candida antactica with efficient perhydrolysis performance by eliminating its hydrolase activity. Sci. Rep. 7, 1\u20135 (2017).","journal-title":"Sci. Rep."},{"key":"18913_CR31","first-page":"1","volume":"1","author":"M Vagnoni","year":"2021","unstructured":"Vagnoni, M. et al. Lipase catalysed oxidations in a sugar-derived natural deep eutectic solvent. Biocatal. Biotrans. 1, 1\u201310 (2021).","journal-title":"Biocatal. Biotrans."},{"key":"18913_CR32","doi-asserted-by":"publisher","first-page":"774","DOI":"10.1002\/ajoc.201402011","volume":"3","author":"Q Li","year":"2014","unstructured":"Li, Q. et al. Enantioselective hydrogenation of the double bond of exocyclic \u03b1, \u03b2-unsaturated carbonyl compounds catalyzed by iridium\/H8-BINOL-derived phosphine-oxazoline complexes. Asian J. Org. Chem. 3, 774\u2013783 (2014).","journal-title":"Asian J. Org. Chem."},{"key":"18913_CR33","doi-asserted-by":"publisher","first-page":"124","DOI":"10.1016\/j.tet.2017.11.045","volume":"74","author":"H Kaku","year":"2018","unstructured":"Kaku, H., Ito, M., Horikawa, M. & Tsunoda, T. Deracemization of \u03b1-monosubstituted cyclopentanones in the presence of a TADDOL-type host molecule. Tetrahedron 74, 124\u2013129 (2018).","journal-title":"Tetrahedron"},{"key":"18913_CR34","doi-asserted-by":"publisher","first-page":"61","DOI":"10.1016\/j.molcatb.2007.12.012","volume":"54","author":"MY Rios","year":"2008","unstructured":"Rios, M. Y., Salazar, E. & Olivo, H. F. Chemo-enzymatic Baeyer\u2013Villiger oxidation of cyclopentanone and substituted cyclopentanones. J. Mol. Catal. B Enzym. 54, 61\u201366 (2008).","journal-title":"J. Mol. Catal. B Enzym."},{"key":"18913_CR35","doi-asserted-by":"publisher","first-page":"3443","DOI":"10.3390\/ma14133443","volume":"14","author":"A Szelwicka","year":"2021","unstructured":"Szelwicka, A. et al. Chemo-enzymatic Baeyer\u2013Villiger oxidation facilitated with lipases immobilized in the supported ionic liquid phase. Materials 14, 3443 (2021).","journal-title":"Materials"},{"issue":"1","key":"18913_CR36","doi-asserted-by":"publisher","first-page":"89","DOI":"10.1039\/P19950000089","volume":"1","author":"SC Lemoult","year":"1995","unstructured":"Lemoult, S. C., Richardson, P. F. & Roberts, S. M. Lipase-catalysed Baeyer\u2013Villiger reactions. J. Chem. Soc. Perkin Trans. 1(1), 89\u201391 (1995).","journal-title":"J. Chem. Soc. Perkin Trans."}],"container-title":["Scientific Reports"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-18913-2.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-18913-2","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-18913-2.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,8,31]],"date-time":"2022-08-31T10:17:55Z","timestamp":1661941075000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-18913-2"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,8,30]]},"references-count":36,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2022,12]]}},"alternative-id":["18913"],"URL":"https:\/\/doi.org\/10.1038\/s41598-022-18913-2","relation":{},"ISSN":["2045-2322"],"issn-type":[{"value":"2045-2322","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,8,30]]},"assertion":[{"value":"6 May 2022","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"22 August 2022","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"30 August 2022","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"The authors declare no competing interests.","order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"14795"}}