Screening primary racemic amines for enantioseparation by derivatized polysaccharide and cyclofructan columns

摘要

It is a challenge to separate the enantiomers of native chiral amines prone to deleterious silanol interactions. Aset of 39 underivatized chiral primary amines was screened for enantiomeric separation. Seven recentlyintroduced commercial chiral columns were tested. They included six polysaccharide based chiral stationaryphases (CSP) with bonded derivatives, ChiralPak? IA, IB, IC, ID, IE and IF columns and a cyclofructanderivatized CSP, Larihc? CF6-P column. Both the normal phase (NP) mode with heptane/alcohol mobile phasesand the polar organic (PO) mode with acetonitrile/alcohol were evaluated. It was found that the cyclofructanbased CSP demonstrated the highest success rate in separating primary amines in the PO mode with only onechiral amine not resolved. It is shown that, when screening the columns, there is no standard optimal condition;an excellent mobile phase composition for one column may be poorly suited to another one. Althoughbutylamine was a good mobile phase additive for the polysaccharide columns in both PO and NP modes, it wasdetrimental to the enantio-recognition capability of the cyclofructan column. Triethylamine was the appropriatesilanol screening agent for this latter column.