Novel Zwitterionic Chiral Ion Exchangers for HPLC-Enantioseparation of Chiral Acids, Amino Acids and Peptides

R. PELL; D. A. BIANCHI; S. WERNISCH; W. LINDNER

Innsbruck

Simposio; 15th Symposium of the Euroanalysis Series; 2009

In this presentation we discuss the consequent structure modificationof the chiral selector motif composed of a chiral cationic site (cinchonane derivative) and ananionic site (amino acid type derivative) which behave synergistically to each other in thecourse of the bonding of complementary chiral selectands. Depending on the pk values of theionic moieties the pH, the buffer type and the strength of the mobile phase will effect theretention and stereoselectivity. From a stereochemical point of view it could be shown that thesulfonic acid moiety of the chiral selectors should be directly linked to a chiral center in orderto fully unfold its potential for an enantioselective ion pairing with an amino group of theselectand. Besides free amino acids a surprisingly good enantioselectivity for chiral peptides could be observed which will also be discussed in this contribution.