Preparation and enzymatic resolution of 3-hydroxy fatty acid nicotinyl esters

Abstract

A general method is presented for the preparation of homochiral 3-hydroxy fatty acid nicotinyl ester. The pyridine moiety of the esters strongly moderates the reactivity of the borane. Incomplete conversion, however, was overcome by Lewis acid catalysis. Additionally, his structural element seems to be responsible for an improvement of the enzymatic resolution compared to the respective alkyl esters. The resolved enantiomers will be the basic material for liposome building molecules of different chirality.

Graphical Abstract

Keywords:

• Boron hydride reduction
• enzymatic resolution
• fatty acid esters
• β-keto esters
• nicotinyl ester

Supporting information

Substance characterization data, Chromatograms, IR spectra, ¹H and ¹³C NMR spectra of the compounds, Chromatograms and data (table 2) of the enzymatic resolution.

Disclosure statement

The authors declare no competing financial interest.