PMID- 20554288 OWN - NLM STAT- MEDLINE DCOM- 20100917 LR - 20131121 IS - 1873-3778 (Electronic) IS - 0021-9673 (Linking) VI - 1217 IP - 30 DP - 2010 Jul 23 TI - Separation of chiral primary amino compounds by forming a sandwiched complex in reversed-phase high performance liquid chromatography. PG - 4965-70 LID - 10.1016/j.chroma.2010.05.053 [doi] AB - 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. CI - Copyright (c) 2010 Elsevier B.V. All rights reserved. FAU - Zhang, Chen AU - Zhang C AD - Global Quality Services-Analytical Science, Schering-Plough Corp., 1011 Morris Avenue, Union, NJ 07083, USA. FAU - Huang, Wei X AU - Huang WX FAU - Chen, Zhi AU - Chen Z FAU - Rustum, Abu M AU - Rustum AM LA - eng PT - Journal Article DEP - 20100602 PL - Netherlands TA - J Chromatogr A JT - Journal of chromatography. A JID - 9318488 RN - 0 (Amino Acids) RN - 0 (Indans) RN - 34698-41-4 (1-aminoindan) RN - 9753I242R5 (1-Naphthylamine) SB - IM MH - 1-Naphthylamine/*chemistry MH - Amino Acids/*chemistry MH - Chromatography, Reverse-Phase/*instrumentation/*methods MH - Indans/*chemistry MH - Stereoisomerism EDAT- 2010/06/18 06:00 MHDA- 2010/09/21 06:00 CRDT- 2010/06/18 06:00 PHST- 2010/02/08 00:00 [received] PHST- 2010/05/21 00:00 [revised] PHST- 2010/05/26 00:00 [accepted] PHST- 2010/06/18 06:00 [entrez] PHST- 2010/06/18 06:00 [pubmed] PHST- 2010/09/21 06:00 [medline] AID - S0021-9673(10)00725-9 [pii] AID - 10.1016/j.chroma.2010.05.053 [doi] PST - ppublish SO - J Chromatogr A. 2010 Jul 23;1217(30):4965-70. doi: 10.1016/j.chroma.2010.05.053. Epub 2010 Jun 2.