Separation of chiral primary amino compounds by forming a sandwiched complex in reversed-phase high performance liquid chromatography.
Separation of chiral primary amino compounds was efficiently achieved under reversed-phase high performance liquid chromatography (RP-HPLC) conditions using a mixture of non-chiral crown ether (18-crown-6) and dimethyl-beta-cyclodextrin (DM-beta-CD) in the mobile phase. Under these conditions, the amino group of the chiral compound was protonated in a low pH mobile phase, and then interacted with 18-crown-6 and DM-beta-CD to form a sandwiched complex [18-crown-6+amine+CD]. Enantiomers of the compound in the sandwiched complex were separated with good enantioselectivity. Formation of the sandwiched complex among the chiral compound and additives in the mobile phase is a key step of the chiral separation. Four different chiral amino compounds namely, 1-aminoindan (AI), 1,2,3,4-tetrahydro-1-naphthylamine (THNA), tyrosine (Tyr), and phenylalanine (Phe), were selected to demonstrate the separation using the sandwiched complex mechanism in RP-HPLC.
Zhang
Chen
C
Global Quality Services-Analytical Science, Schering-Plough Corp., 1011 Morris Avenue, Union, NJ 07083, USA.
Huang
Wei X
WX
Chen
Zhi
Z
Rustum
Abu M
AM
D015057:1-Naphthylamine / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D056148:Chromatography, Reverse-Phase / Q000295:instrumentation* / Q000379:methods*; D007189:Indans / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D007189:Indans; C016992:1-aminoindan; D015057:1-Naphthylamine