Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71
Özet
Enantiopure benzo-fused cyclic alcohols have been used as a building block of a drug for Parkinson’s disease. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of seven lactic acid bacteria (LAB) strains were investigated as whole-cell biocatalyst in the enantioselective reduction of 1-indanone (1). Lactobacillus paracasei BD71 was found to have the best reductive capacity. Effects of different parameters such as pH, incubation time, agitation speed and temperature, on enantiomeric excess (ee) and conversion were investigated in a bioconversion. (S)-1-indanol ((S)-2) could be used as precursor for the synthesis of rasagiline mesylate TVP1012 for the therapy of Parkinson’s illness. It was produced in gram-scale (5.24 g), high yield (93%) and enantiomerically pure form using L. paracasei BD71 whole-cell biocatalysts. Also, to our knowledge, this is the first report on production of (S)-2 using whole-cell catalyst in enantiopure form, excellent yield, conversion and gram scale. This is a cheap, clean and eco-friendly process for production of (S)-2 compared to chemical processes.
Anahtar Kelimeler
- Scopus
- 6
- WoS
- 6
- OpenAlex
- 6
Tam Kayıt
| Alan | Değer | Dil |
|---|---|---|
| dc.contributor.author | Kalay, Erbay | |
| dc.contributor.author | Dertli, Enes | |
| dc.contributor.author | Şahin, Engin | |
| dc.date.accessioned | 2026-10-29T19:09:06.127408860Z | |
| dc.date.available | 2026-10-29T19:09:06.127408860Z | |
| dc.date.issued | 2022 | |
| dc.description.abstract | Enantiopure benzo-fused cyclic alcohols have been used as a building block of a drug for Parkinson’s disease. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of seven lactic acid bacteria (LAB) strains were investigated as whole-cell biocatalyst in the enantioselective reduction of 1-indanone (1). Lactobacillus paracasei BD71 was found to have the best reductive capacity. Effects of different parameters such as pH, incubation time, agitation speed and temperature, on enantiomeric excess (ee) and conversion were investigated in a bioconversion. (S)-1-indanol ((S)-2) could be used as precursor for the synthesis of rasagiline mesylate TVP1012 for the therapy of Parkinson’s illness. It was produced in gram-scale (5.24 g), high yield (93%) and enantiomerically pure form using L. paracasei BD71 whole-cell biocatalysts. Also, to our knowledge, this is the first report on production of (S)-2 using whole-cell catalyst in enantiopure form, excellent yield, conversion and gram scale. This is a cheap, clean and eco-friendly process for production of (S)-2 compared to chemical processes. | |
| dc.identifier.doi | 10.1080/10242422.2021.2004133 | |
| dc.identifier.eissn | 1029-2446 | |
| dc.identifier.endpage | 392 | |
| dc.identifier.issn | 1024-2422 | |
| dc.identifier.issue | 5 | |
| dc.identifier.scopus | 2-s2.0-85119347087 | |
| dc.identifier.startpage | 386 | |
| dc.identifier.uri | https://rdlopen.rawdatalibrary.net/r/bayburt/12031 | |
| dc.identifier.volume | 40 | |
| dc.identifier.wos | WOS:000719228000001 | |
| dc.language.iso | en | |
| dc.publisher | Taylor and Francis Ltd. | |
| dc.relation.ispartof | Biocatalysis and Biotransformation | |
| dc.rights | info:eu-repo/semantics/closedAccess | |
| dc.subject | (S)-1-indanol | |
| dc.subject | Biotransformation | |
| dc.subject | Lactobacillus paracasei BD71 | |
| dc.subject | Parkinson’s drug precursor | |
| dc.subject | whole-cell biocatalysts | |
| dc.subject.classification | Biochemistry & Molecular Biology | |
| dc.subject.classification | Biotechnology & Applied Microbiology | |
| dc.subject.other | Bacilli | |
| dc.subject.other | Cells | |
| dc.subject.other | Cytology | |
| dc.subject.other | Enantiomers | |
| dc.subject.other | Enzymes | |
| dc.subject.other | Ketones | |
| dc.subject.other | 1 indanone | |
| dc.subject.other | ketone | |
| dc.subject.other | rasagiline | |
| dc.subject.other | unclassified drug | |
| dc.subject.other | (S)-1-indanol | |
| dc.subject.other | Asymmetric synthesis | |
| dc.subject.other | Building blockes | |
| dc.subject.other | Cyclic alcohols | |
| dc.subject.other | Enantiopure | |
| dc.subject.other | Gram scale | |
| dc.subject.other | Indanol | |
| dc.subject.other | Lactobacillus paracasei bd71 | |
| dc.subject.other | Parkinson’s drug precursor | |
| dc.subject.other | Whole cell biocatalysts | |
| dc.subject.other | agitation | |
| dc.subject.other | Article | |
| dc.subject.other | bacterial strain | |
| dc.subject.other | bacterium culture | |
| dc.subject.other | bacterium isolation | |
| dc.subject.other | biocatalysis | |
| dc.subject.other | biotransformation | |
| dc.subject.other | carbon nuclear magnetic resonance | |
| dc.subject.other | chemical phenomena | |
| dc.subject.other | chiral chromatography | |
| dc.subject.other | column chromatography | |
| dc.subject.other | controlled study | |
| dc.subject.other | drug structure | |
| dc.subject.other | enantiomeric excess | |
| dc.subject.other | enantioselectivity | |
| dc.subject.other | Enterococcus faecium | |
| dc.subject.other | enzyme activity | |
| dc.subject.other | flow rate | |
| dc.subject.other | high performance liquid chromatography | |
| dc.subject.other | incubation time | |
| dc.subject.other | lactic acid bacterium | |
| dc.subject.other | Lactobacillus fermentum | |
| dc.subject.other | Lactobacillus paracasei | |
| dc.subject.other | Lactobacillus plantarum | |
| dc.subject.other | nonhuman | |
| dc.subject.other | pH | |
| dc.subject.other | proton nuclear magnetic resonance | |
| dc.subject.other | temperature | |
| dc.subject.other | thin layer chromatography | |
| dc.subject.other | Lactic acid | |
| dc.title | Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71 | |
| dc.type | Article | |
| rdl.citation.openalex | 6 | |
| rdl.citation.scopus | 6 | |
| rdl.citation.wos | 6 | |
| rdl.oa.status | closed | |
| rdl.scopus.quartile | Q3 | |
| rdl.sdg | SDG03 | |
| rdl.source.index | SCOPUS | |
| rdl.source.index | WOS | |
| rdl.wos.index | Science Citation Index Expanded (SCI-EXPANDED) |

