Racemic 1,3-amino alcohols were resolved via lipase-catalysed O-acylation of their Z derivatives, using vinyl butyrate in different ethers as solvents. In accordance with the empirical rule, most of the screened lipases preferred the 1S enantiomer. In order to monitor the enzymatic reactions a high-performance liquid chromatographic method was developed. The applied chiral stationary phase (Chiralcel OD) allowed simultaneous separation of all the four isomers which were present in the reaction mixture. Retention mechanisms of alcohol and ester analogues were investigated in detail. Besides the direct way, indirect separation involving precolumn derivatization with 1-fluoro-2,4-dinitrophenyl-5-L-alaninamide permitted the differentiation of 1,3-amino alcohol enantiomers with high resolution. In combination with the addition of standards, both direct and indirect methods can be used to identify absolute configurations and hence to determine the enzyme selectivity.
|Translated title of the contribution||Chiral discrimination of cyclic 1,3-amino alcohol enantiomers|
|Number of pages||10|
|Journal||Magyar Kemiai Folyoirat, Kemiai Kozlemenyek|
|Publication status||Published - febr. 1 1999|
ASJC Scopus subject areas