Green synthesis of chiral aromatic alcohols with Lactobacillus kefiri P2 as a novel biocatalyst

Baydaş Y., Dertli E., Şahin E.

SYNTHETIC COMMUNICATIONS, cilt.50, sa.7, ss.1035-1045, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 50 Sayı: 7
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1080/00397911.2020.1729809
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, EMBASE
  • Sayfa Sayıları: ss.1035-1045
  • Anahtar Kelimeler: Asymmetric synthesis, aromatic ketones, bioreduction, Lactobacillus kefiri, whole cell, ASYMMETRIC REDUCTION, CARBONYL REDUCTASE, DEHYDROGENASE, ACETOPHENONE, KETONES, CELLS
  • Yıldız Teknik Üniversitesi Adresli: Evet

Özet

Biocatalytic reduction is a very important field of research in synthetic organic chemistry. Herein, three different Lactic Acid Bacteria (LAB) strains were evaluated for their bioreduction potential using acetophenone as a model substrate. Among these strains, Lactobacillus kefiri P2 strain was determined as the best asymmetric reduction biocatalyst. Reaction optimization parameters such as reaction time, temperature, agitation speed and pH were systematically optimized using Lactobacillus kefiri P2 strain and model substrate acetophenone. Under these optimized reaction conditions, secondary chiral alcohols were obtained by bioreduction of various prochiral ketones with results up to 99% enantiomeric excess. In addition, the steric and electronic effects of substituents on enantioselectivity and conversion were evaluated. It has been shown that Lactobacillus kefiri P2 biocatalyst was an effective catalyst for asymmetric reduction. This method provides an environmentally friendly method for the synthesis of optically pure alcohols and an alternative approach to chemical catalysts.