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


Yildiz T. , Yusufoglu A.

TETRAHEDRON-ASYMMETRY, cilt.22, ss.1347-1352, 2011 (SCI İndekslerine Giren Dergi)

  • Cilt numarası: 22 Konu: 12
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1016/j.tetasy.2011.07.017
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Sayfa Sayısı: ss.1347-1352

Özet

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.

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 4a4z with an (R)-configuration and high enantiomeric excess (∼100%). The corresponding ketones 1a1z were synthesized and then reduced with NaBH4 to their racemic alcohols 2a2z, which were converted into their racemic acetyl derivatives 3a3z. Enzymes of four different types were used for the enantioselective hydrolysis of these acetyl compounds 3a3z. The optimal reaction conditions for these four enzymes were established by investigating the enantiomeric excesses by chiral HPLC. AmanolipasefromBurkholdericacepacia(PseudomonascepaciaAL-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 carbinols4a4z.