Direct high-performance liquid chromatographic separation of the enantiomers of an aromatic amine and four aminoalcohols using polysaccharide chiral stationary phases and acidic additive.
The HPLC enantiomeric separation of N-benzyl-alpha-methyl-benzylamine, phenylalaninol, tryptophanol, 2 (diphenylhydroxymethyl)pyrrolidine, and isoproterenol was accomplished in the normal-phase mode using two polysaccharide-derived chiral stationary phases (CSPs) and various n-hexane/2-propanol mobile phases with acidic (TFA) or basic (DEA) additive. The compounds were separated without any derivatization and separation factor range between 2.09 and 1.09 with resolution factor 3.4 and 0.4, respectively. The best separation of the enantiomers of the amine was achieved on amylose tris (3, 5-dimethylphenylcarbamate) CSP with TFA additive in the mobile phase; in acidic conditions, instead, the best enantioseparation of the aminoalcohols was achieved on cellulose tris (3, 5-dimethylphenilcarbamate). A long equilibration time of the CSP when switching from an undoped mobile phase to a doped one is required to obtain reproducible results.
Caccamese
Salvatore
S
Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, Catania, Italy. scaccamese@dipchi.unict.it
Bianca
Salvatore
S
Carter
Guy T
GT
D000143:Acids; D000588:Amines / Q000737:chemistry / Q000302:isolation & purification*; D000605:Amino Alcohols / Q000737:chemistry / Q000302:isolation & purification*; D001589:Benzphetamine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D007545:Isoproterenol / Q000737:chemistry / Q000302:isolation & purification; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D011134:Polysaccharides; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification
D000143:Acids; D000588:Amines; D000605:Amino Alcohols; D011134:Polysaccharides; D011759:Pyrrolidines; D001589:Benzphetamine; C008669:norbenzphetamine; C012481:phenylalaninol; D010649:Phenylalanine; C069544:tryptophanol; D014364:Tryptophan; D007545:Isoproterenol