Enantio- and diastereoselective acylation of prochiral hydroxyl group of pyrimidine acyclonucleosides

The transesterification reaction of series pyrimidine acyclonucleosides was carried out with lipase (EC 3.1.13) Amano PS from Burkholderia cepacia (BCL) as biocatalyst. The BCL-mediated acylation of prochiral groups of diols produced the corresponding monoesters in high yield and with enantiomeric/diasteromeric excess from 77 to 99%. The lipase BCL enabled desymmetrization of pro-R hydroxyl groups and gave (2R)-monoesters. Absolute configuration of the products was confirmed by means of ECD spectroscopy supported by theoretical calculations. (C) 2016 Elsevier B.V. All rights reserved.