Synthesis of Chiral 1,3-keto-acetates through Enzymatic Kinetic Resolution with Amano Lipase from Pseudomonas fluorescens

Can H. C., YILDIZ T., ÇELİK ONAR H.

ChemistrySelect, cilt.5, sa.25, ss.7543-7547, 2020 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 5 Sayı: 25
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1002/slct.202001987
  • Dergi Adı: ChemistrySelect
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.7543-7547
  • Anahtar Kelimeler: Amano lipase, biocatalyst, chiral 1,3-keto acetates, kinetic resolution, transesterification
  • İstanbul Kent Üniversitesi Adresli: Hayır

Özet

This study provides an enzymatic kinetic resolution (EKR) method for the biocatalytic enantioselective synthesis of chiral β-keto acetates. For the first time, the attitude of several lipase enzymes has been examined under different conditions for the EKR of the racemic 1,3-keto alcohols. We found that the Amano lipase from Pseudomonas fluorescens (AL-PF) lipase showed the best results for the resolution of the racemic 1,3-keto alcohols. We developed a highly effective EKR method by changing the enzyme, temperature, solvent, and enzyme amount in order to synthesize the chiral 1,3-keto esters, which are useful intermediates in organic synthesis. This study presents an efficient method for the synthesis of 1,3-keto acetates with a good yield and high enantioselectivity with the R configuration.