Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71

Kalay E., DERTLİ E., ŞAHİN E.

BIOCATALYSIS AND BIOTRANSFORMATION, cilt.40, sa.5, ss.386-392, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 40 Sayı: 5
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1080/10242422.2021.2004133
  • Dergi Adı: BIOCATALYSIS AND BIOTRANSFORMATION
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Compendex, EMBASE, Environment Index, Food Science & Technology Abstracts
  • Sayfa Sayıları: ss.386-392
  • Anahtar Kelimeler: Biotransformation, (S)-1-indanol, Parkinson's drug precursor, whole-cell biocatalysts, Lactobacillus paracasei BD71, ENANTIOMERICALLY PURE, REDUCTION, KETONES, HYDROGENATION, ALCOHOL
  • Yıldız Teknik Üniversitesi Adresli: Evet

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.