Efficient bioreduction of 4-phenyl-2-butanone to drug precursor (S)-4-phenyl-2-butanol by a whole-cell biocatalyst using a novel hybrid design technique

MakaleAçık ErişimScopus SJRQ1

Özet

Asymmetric synthesis is a critical tactic in pharmaceutical industries for creating chiral medications as it allows an enantiomer to be obtained in synthetic chemistry. The asymmetric bioreduction processes by biocatalysts have shown significant potential in producing chiral alcohols. The amount of substrate and the production method of the biocatalytic synthesis of (S)-4-phenyl-2-butanol ((S)-2) are not still desired levels. Furthermore, the biocatalytic asymmetric reduction of 4-phenyl-2-butanone (1) to (R)- or (S)-4-phenyl-2-butanol did not use any mathematical modeling techniques. In this study, the asymmetric bioreduction of 1 was carried out in this work employing Lactobacillus paracasei BD71 biocatalyst and a novel hybrid design-based optimization approach. By using the hybrid design technique, the optimal circumstances were discovered to be pH = 7, temperature = 29 °C, incubation period = 66 h, and agitation speed = 189 rpm. Also, the enantiomeric excess (ee) and conversion could be 99.15 % and 98.19 %, respectively. Next, (S)-2 was acquired to be ee: 99 %, conversion: >99 %, and yield: 97 % from the optimum bioreduction conditions. Furthermore, 14.08 g of 1 under optimal conditions was entirely transformed into (S)-2 (13.84 g, 97 % isolated yield). This study is the first research attempt to use a biocatalyst and an innovative and new hybrid design-based optimization approach to fabricate enantiopure (S)-2 at a high gram scale. This work has successfully demonstrated that the new hybrid design-based optimization technique is applicable to biocatalytic asymmetric reduction processes.

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https://rdlopen.rawdatalibrary.net/r/bayburt/13028Resmi atıflarda kullanılan kalıcı adres
DOI
https://doi.org/10.1016/j.mcat.2024.114289Yayıncı resmi DOI adresi
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9
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8
OpenAlex
5
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Tam Kayıt
AlanDeğerDil
dc.contributor.authorBayhan, Beyzanur
dc.contributor.authorÖzdemir, Akın
dc.contributor.authorDertli, Enes
dc.contributor.authorŞahin, Engin
dc.date.accessioned2026-10-29T19:10:22.553646071Z
dc.date.available2026-10-29T19:10:22.553646071Z
dc.date.issued2024
dc.description.abstractAsymmetric synthesis is a critical tactic in pharmaceutical industries for creating chiral medications as it allows an enantiomer to be obtained in synthetic chemistry. The asymmetric bioreduction processes by biocatalysts have shown significant potential in producing chiral alcohols. The amount of substrate and the production method of the biocatalytic synthesis of (S)-4-phenyl-2-butanol ((S)-2) are not still desired levels. Furthermore, the biocatalytic asymmetric reduction of 4-phenyl-2-butanone (1) to (R)- or (S)-4-phenyl-2-butanol did not use any mathematical modeling techniques. In this study, the asymmetric bioreduction of 1 was carried out in this work employing Lactobacillus paracasei BD71 biocatalyst and a novel hybrid design-based optimization approach. By using the hybrid design technique, the optimal circumstances were discovered to be pH = 7, temperature = 29 °C, incubation period = 66 h, and agitation speed = 189 rpm. Also, the enantiomeric excess (ee) and conversion could be 99.15 % and 98.19 %, respectively. Next, (S)-2 was acquired to be ee: 99 %, conversion: >99 %, and yield: 97 % from the optimum bioreduction conditions. Furthermore, 14.08 g of 1 under optimal conditions was entirely transformed into (S)-2 (13.84 g, 97 % isolated yield). This study is the first research attempt to use a biocatalyst and an innovative and new hybrid design-based optimization approach to fabricate enantiopure (S)-2 at a high gram scale. This work has successfully demonstrated that the new hybrid design-based optimization technique is applicable to biocatalytic asymmetric reduction processes.
dc.identifier.articlenumber114289
dc.identifier.doi10.1016/j.mcat.2024.114289
dc.identifier.issn2468-8231
dc.identifier.scopus2-s2.0-85195290337
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/bayburt/13028
dc.identifier.volume564
dc.identifier.wosWOS:001286759900001
dc.language.isoen
dc.publisherElsevier B.V.
dc.relation.ispartofMolecular Catalysis
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject(s)-4-phenyl-2-butanol
dc.subjectAsymmetric bioreduction
dc.subjectBiocatalysts
dc.subjectDrug precursor
dc.subjectGreen chemistry
dc.subject.classificationChemistry, Physical
dc.subject.classificationChemistry
dc.subject.otherEnantiomers
dc.subject.otherEnzymes
dc.subject.otherStereochemistry
dc.subject.otherSubstrates
dc.subject.other(s)-4-phenyl-2-butanol
dc.subject.other2-butanol
dc.subject.other2-butanone
dc.subject.otherAsymmetric bioreduction
dc.subject.otherAsymmetric reduction
dc.subject.otherBioreductions
dc.subject.otherDesign technique
dc.subject.otherDrug precursor
dc.subject.otherGreen-chemistry
dc.subject.otherHybrid design
dc.subject.otherSustainable chemistry
dc.titleEfficient bioreduction of 4-phenyl-2-butanone to drug precursor (S)-4-phenyl-2-butanol by a whole-cell biocatalyst using a novel hybrid design technique
dc.typeArticle
rdl.citation.openalex5
rdl.citation.scopus9
rdl.citation.wos8
rdl.oa.statusclosed
rdl.oa.statusgreen
rdl.oa.urlhttp://hdl.handle.net/20.500.12403/3256
rdl.scopus.quartileQ1
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)