Effective biocatalytic synthesis of enentiopure (R)-1,2-diphenylethanol as a pharmaceutical precursor using whole-cell biocatalyst

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Özet

Optically active alcohols are crucial precursors. 1,2-Diarylethanols and their analogues constitute a significant group of substances of biological significance. The biocatalytic synthesis of (R)-1,2-diphenylethanol ((R)-2), which can be utilized as a precursor to important drugs, is still not at the desired level in terms of substrate amount and production process. This study asymmetrically reduced 1,2-diphenylethanone (1) using the Lactobacillus paracasei BD87E6 biocatalyst and a novel orthogonal quadratic design-embedded optimization approach. The following reaction optimization conditions were determined using the suggested optimization technique: pH = 6, temperature = 31 °C, incubation period = 48 h, and agitation speed=134 rpm. In addition, the reaction conversion was estimated to be 99.38 %, and the product's enantiomeric excess (ee) was estimated to be 99.12 %. Further, (R)-2 was produced with >99 % ee, >99 % conversion, and 98 % yield in the experimental investigation under the established optimum conditions. This study is the first attempt to reduce substrate 1 to (R) or (S)-2 using a mathematical optimization method in the presence of a biocatalyst. Furthermore, on a high-gram scale, 1 (15.70 g) was entirely transformed into (R)-2 (15.54 g, 98 % isolated yield). Notably, this study is also the first to perform the gram-scale production of (R)-2 using a novel optimization approach and a biocatalyst. Finally, the innovative and novel orthogonal quadratic design-embedded optimization technique has been demonstrated as an efficient, cost-effective, and environmentally friendly biocatalytic procedure for synthesizing (R)-2.

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https://rdlopen.rawdatalibrary.net/r/bayburt/11638Resmi atıflarda kullanılan kalıcı adres
DOI
https://doi.org/10.1016/j.mcat.2024.114257Yayıncı resmi DOI adresi
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Tam Kayıt
AlanDeğerDil
dc.contributor.authorÇakmak, Fadile
dc.contributor.authorÖzdemir, Akın
dc.contributor.authorDertli, Enes
dc.contributor.authorŞahin, Engin
dc.date.accessioned2026-10-29T19:08:37.555232766Z
dc.date.available2026-10-29T19:08:37.555232766Z
dc.date.issued2024
dc.description.abstractOptically active alcohols are crucial precursors. 1,2-Diarylethanols and their analogues constitute a significant group of substances of biological significance. The biocatalytic synthesis of (R)-1,2-diphenylethanol ((R)-2), which can be utilized as a precursor to important drugs, is still not at the desired level in terms of substrate amount and production process. This study asymmetrically reduced 1,2-diphenylethanone (1) using the Lactobacillus paracasei BD87E6 biocatalyst and a novel orthogonal quadratic design-embedded optimization approach. The following reaction optimization conditions were determined using the suggested optimization technique: pH = 6, temperature = 31 °C, incubation period = 48 h, and agitation speed=134 rpm. In addition, the reaction conversion was estimated to be 99.38 %, and the product's enantiomeric excess (ee) was estimated to be 99.12 %. Further, (R)-2 was produced with >99 % ee, >99 % conversion, and 98 % yield in the experimental investigation under the established optimum conditions. This study is the first attempt to reduce substrate 1 to (R) or (S)-2 using a mathematical optimization method in the presence of a biocatalyst. Furthermore, on a high-gram scale, 1 (15.70 g) was entirely transformed into (R)-2 (15.54 g, 98 % isolated yield). Notably, this study is also the first to perform the gram-scale production of (R)-2 using a novel optimization approach and a biocatalyst. Finally, the innovative and novel orthogonal quadratic design-embedded optimization technique has been demonstrated as an efficient, cost-effective, and environmentally friendly biocatalytic procedure for synthesizing (R)-2.
dc.identifier.articlenumber114257
dc.identifier.doi10.1016/j.mcat.2024.114257
dc.identifier.issn2468-8231
dc.identifier.scopus2-s2.0-85194141247
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/bayburt/11638
dc.identifier.volume563
dc.identifier.wosWOS:001249755100001
dc.language.isoen
dc.publisherElsevier B.V.
dc.relation.ispartofMolecular Catalysis
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject(R)-1,2-diphenylethanol
dc.subjectAsymmetric reduction
dc.subjectBiocatalyst
dc.subjectDrug precursor
dc.subjectGreen chemistry
dc.subject.classificationChemistry, Physical
dc.subject.classificationChemistry
dc.subject.otherBiocatalysts
dc.subject.otherCost effectiveness
dc.subject.otherOptimization
dc.subject.otherSubstrates
dc.subject.other(R)-1,2-diphenylethanol
dc.subject.otherAsymmetric reduction
dc.subject.otherBiocatalytic synthesis
dc.subject.otherDiphenylethanol
dc.subject.otherDrug precursor
dc.subject.otherEmbedded optimizations
dc.subject.otherEnantiomeric excess
dc.subject.otherGreen-chemistry
dc.subject.otherOptimization approach
dc.subject.otherOptimization techniques
dc.subject.otherSustainable chemistry
dc.titleEffective biocatalytic synthesis of enentiopure (R)-1,2-diphenylethanol as a pharmaceutical precursor using whole-cell biocatalyst
dc.typeArticle
rdl.citation.openalex6
rdl.citation.scopus7
rdl.citation.wos7
rdl.oa.statusclosed
rdl.scopus.quartileQ1
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)