Chiral discrimination of primary amines by HPLC after labeling with a chiral derivatization reagent, trans-2-(2,3-anthracenedicarboximido)-cyclohexanecarbonyl chloride.
Enantiomeric discrimination of chiral primary amines was performed by both reversed-phase HPLC and normal-phase HPLC after labeling with a chiral fluorescent derivatization reagent, (1R,2R)- and (1S,2S)-trans-2-(2,3-anthracenedicarboximido)cyclohexanecarbonyl chloride. Use of HPLC permits separation of diastereomeric derivatives of amines up to C30 which have a primary amino group at the middle of the alkyl chain. The derivatives of primary amines having an anteiso alkyl chain, which has a chiral branched-methyl at the n-3 position of the alkyl chain, were also separated by HPLC, and it was also possible to separate niphatesine D by reversed-phase HPLC after derivatization.
Akasaka
Kazuaki
K
Graduate School of Life Sciences, Tohoku University, Sendai, Japan. akasaka@biochem.tohoku.ac.jp
Ohtaki
Takashi
T
Ohrui
Hiroshi
H
D000473:Alkanes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D000873:Anthracenes / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D003510:Cyclohexanes / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism
D000473:Alkanes; D000588:Amines; D000873:Anthracenes; D002712:Chlorides; D003510:Cyclohexanes; D011725:Pyridines; C506365:Cyclohexane