Capillary zone electrophoresis study of naphthylethylcarbamoylated beta-cyclodextrins.
Regiospecifically monosubstituted 1-(1-naphthyl)ethylcarbamoylated beta-cyclodextrins (NEC-beta-CDs) were successfully employed as chiral additives in capillary zone electrophoresis (CZE) to achieve chiral separation of N-(3,5-dinitrobenzoyl)phenylglycine (3,5-DNB-PG), phenylalanine (3,5-DNB-PA), and homophenylalanine (3,5-DNB-HPA). The enantioselectivity of the various site-substituted NEC-beta-CDs in CZE was compared with that of native beta-CD. Complexation constants of the three 3,5-DNB amino acids with beta-CD were determined from the CZE results: 3,5-DNB-L-HPA, 473 +/- 9 M-1; 3,5-DNB-D-HPA, 460 +/- 10 M-1; 3,5-DNB-L-PA, 260 +/- 4 M-1; 3,5-DNB-D-PA, 161 +/- 3 M-1; and 3,5-DNB-D, L-PG, 43 +/- 4 M-1.
Gahm
K H
KH
Department of Chemistry, University of Hawaii at Manoa, Honolulu 96822.
Stalcup
A M
AM
D000613:Aminobutyrates / Q000737:chemistry / Q000302:isolation & purification; D002219:Carbamates / Q000032:analysis*; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003505:Cyclodextrins / Q000032:analysis*; D004586:Electrophoresis / Q000379:methods*; D005998:Glycine / Q000031:analogs & derivatives / Q000302:isolation & purification; D008969:Molecular Sequence Data; D009579:Nitrobenzoates / Q000302:isolation & purification; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000302:isolation & purification; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
C075235:(1-naphthylethyl)carbamoyl beta-cyclodextrin; D000613:Aminobutyrates; D002219:Carbamates; D003505:Cyclodextrins; D009579:Nitrobenzoates; D047392:beta-Cyclodextrins; D010649:Phenylalanine; C051871:N-(3,5-dinitrobenzoyl)phenylglycine; C014328:2-amino-4-phenylbutyric acid; D005998:Glycine