Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution

Yildiz T., Yusufoglu A. S.

TETRAHEDRON-ASYMMETRY, vol.22, no.12, pp.1347-1352, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 12
  • Publication Date: 2011
  • Doi Number: 10.1016/j.tetasy.2011.07.017
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1347-1352
  • Istanbul University Affiliated: Yes

Abstract

The present study deals with the biocatalytic enantioselective synthesis of 19 new chiral alcohols with alkyl (C11–C19) and phenyl, substituted phenyl, heteroaromatic, and naphthyl groups 4a–4z with an (R)-configuration and high enantiomeric excess (∼100%). The corresponding ketones 1a–1z were synthesized and then reduced with NaBH4 to their racemic alcohols 2a–2z, which were converted into their racemic acetyl derivatives 3a–3z. Enzymes of four different types were used for the enantioselective hydrolysis of these acetyl compounds 3a–3z. The optimal reaction conditions for these four enzymes were established by investigating the enantiomeric excesses by chiral HPLC. AmanolipasefromBurkholdericacepacia(Pseudomonascepacia) AL-PS was determined as the best enzyme in this work. This study presents an environmentally friendly and green chemistry method for the synthesis of these new (R)-chiral carbinols4a–4z.

The present study deals with the biocatalytic enantioselective synthesis of 19 new chiral alcohols with alkyl (C(11)-C(19)) and phenyl, substituted phenyl, heteroaromatic, and naphthyl groups 4a-4z with an (R)-configuration and high enantiomeric excess (similar to 100%). The corresponding ketones 1a-1z were synthesized and then reduced with NaBH(4) to their racemic alcohols 2a-2z, which were converted into their racemic acetyl derivatives 3a-3z. Enzymes of four different types were used for the enantioselective hydrolysis of these acetyl compounds 3a-3z. The optimal reaction conditions for these four enzymes were established by investigating the enantiomeric excesses by chiral HPLC. Amano lipase from Burkholderica cepacia (Pseudomonas cepacia) AL-PS was determined as the best enzyme in this work This study presents an environmentally friendly and green chemistry method for the synthesis of these new (R)-chiral carbinols 4a-4z. (C) 2011 Elsevier Ltd. All rights reserved.