Unusual resolution of N-(3,5-dinitrobenzoyl)-alpha-amino acids on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.
While HPLC chiral stationary phases (CSPs) based on chiral crown ethers have been known useful for the resolution of only racemic primary amino compounds or some secondary amino compounds, in this study, we first demonstrated that the CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid is also useful for the resolution of N-benzoyl-alpha-amino acids, which do not contain a primary or secondary amino group. Especially, N-(3,5-dinitrobenzoyl)-alpha-amino acids were resolved better than corresponding N-(3-nitrobenzoyl)- or N-benzoyl-alpha-amino acids, the separation (alpha) and the resolution factors (R(S)) for the resolution of eight N-(3,5-dinitrobenzoyl)-alpha-amino acids being in the range of 1.06-1.81 and 0.54-2.81, respectively. The optimum mobile phase condition was the mixture of acetic acid-triethylamine-acetonitrile with the ratio of 0.05/0.25/100 (v/v/v).
Hyun
Myung Ho
MH
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Kuemjeong-Ku, Busan 609-735, South Korea. mhhyun@pusan.ac.kr
Tan
Guanghui
G
Xue
Jin Ying
JY
D019342:Acetic Acid / Q000737:chemistry; D000097:Acetonitriles / Q000737:chemistry; D000596:Amino Acids / Q000032:analysis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry; D015394:Molecular Structure; D009579:Nitrobenzoates / Q000737:chemistry*; D015203:Reproducibility of Results
D000097:Acetonitriles; D000596:Amino Acids; D043844:Crown Ethers; D005021:Ethylamines; D009579:Nitrobenzoates; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid; D019342:Acetic Acid; C016162:triethylamine; C032159:acetonitrile