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

By Renata Kołodziejska, Marcin Kwit, Renata Studzińska, Maciej Jelecki

July 28, 2017

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Title

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

Author

Renata Kołodziejska, Marcin Kwit, Renata Studzińska, Maciej Jelecki

Year

2016

Journal

Journal of Molecular Catalysis B: Enzymatic

Abstract

The transesterification reaction of series pyrimidine acyclonucleosides was carried out with lipase (EC 3.1.1.3) 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.

Full Article

http://www.sciencedirect.com/science/article/pii/S1381117716301369

Instrument

J-810

Keywords

Circular dichroism, Absolute configuration, Medicinal