Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)-cyclohexyl(phenyl)methanol
Özet
In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)-cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)-cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)-cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale.
Anahtar Kelimeler
- Scopus
- 39
- WoS
- 37
Tam Kayıt
| Alan | Değer | Dil |
|---|---|---|
| dc.contributor.author | Şahin, Engin | |
| dc.contributor.author | Serencam, Hüseyin | |
| dc.contributor.author | Dertli, Enes | |
| dc.date.accessioned | 2026-10-29T19:09:26.015193023Z | |
| dc.date.available | 2026-10-29T19:09:26.015193023Z | |
| dc.date.issued | 2019 | |
| dc.description.abstract | In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)-cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)-cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)-cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale. | |
| dc.description.sponsorship | Bayburt University | |
| dc.identifier.doi | 10.1002/chir.23048 | |
| dc.identifier.eissn | 1520-636X | |
| dc.identifier.endpage | 218 | |
| dc.identifier.issn | 0899-0042 | |
| dc.identifier.issue | 3 | |
| dc.identifier.pmid | 30633374 | |
| dc.identifier.scopus | 2-s2.0-85059887557 | |
| dc.identifier.startpage | 211 | |
| dc.identifier.uri | https://rdlopen.rawdatalibrary.net/r/bayburt/12315 | |
| dc.identifier.volume | 31 | |
| dc.identifier.wos | WOS:000458827600006 | |
| dc.language.iso | en | |
| dc.publisher | John Wiley and Sons Inc. | |
| dc.relation.ispartof | Chirality | |
| dc.rights | info:eu-repo/semantics/openAccess | |
| dc.subject | asymmetric reduction | |
| dc.subject | biocatalyst | |
| dc.subject | biotransformations | |
| dc.subject | chiral aryl methanols | |
| dc.subject | enantioselectivity | |
| dc.subject.classification | Chemistry, Medicinal | |
| dc.subject.classification | Chemistry, Analytical | |
| dc.subject.classification | Chemistry, Organic | |
| dc.subject.classification | Pharmacology & Pharmacy | |
| dc.subject.classification | Chemistry | |
| dc.subject.other | alcohol derivative | |
| dc.subject.other | cyclohexane derivative | |
| dc.subject.other | ketone derivative | |
| dc.subject.other | methanol | |
| dc.subject.other | phenyl group | |
| dc.subject.other | reducing agent | |
| dc.subject.other | bacterial cell | |
| dc.subject.other | bacterial strain | |
| dc.subject.other | biocatalyst | |
| dc.subject.other | biotransformation | |
| dc.subject.other | enantiomer | |
| dc.subject.other | enantioselectivity | |
| dc.subject.other | Enterococcus faecium | |
| dc.subject.other | high performance liquid chromatography | |
| dc.subject.other | incubation time | |
| dc.subject.other | Lactobacillus fermentum | |
| dc.subject.other | Lactobacillus paracasei | |
| dc.subject.other | Lactobacillus plantarum | |
| dc.subject.other | Leuconostoc mesenteroides | |
| dc.subject.other | nonhuman | |
| dc.subject.other | pH | |
| dc.subject.other | priority journal | |
| dc.subject.other | reaction temperature | |
| dc.subject.other | reduction (chemistry) | |
| dc.subject.other | shear stress | |
| dc.subject.other | substrate concentration | |
| dc.subject.other | thin layer chromatography | |
| dc.subject.other | Weissella | |
| dc.subject.other | Weissella cibaria | |
| dc.subject.other | Weissella paramesenteroides | |
| dc.subject.other | whole cell | |
| dc.title | Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)-cyclohexyl(phenyl)methanol | |
| dc.type | Article | |
| rdl.citation.scopus | 39 | |
| rdl.citation.wos | 37 | |
| rdl.department | Department of Food Engineering, Faculty of Engineering, Bayburt University, Bayburt, Turkey | |
| rdl.oa.status | closed | |
| rdl.oa.status | green | |
| rdl.oa.url | https://hdl.handle.net/20.500.12403/306 | |
| rdl.scopus.quartile | Q3 | |
| rdl.source.index | SCOPUS | |
| rdl.source.index | WOS | |
| rdl.source.index | PUBMED | |
| rdl.wos.index | Science Citation Index Expanded (SCI-EXPANDED) |
