Preparation and Evaluation of a Novel 6-mono-Nitrophenylamino-β-cyclodextrin Bonded SBA-15 Chiral Stationary Phase for HPLC†

doi:10.7503/cjcu20140131

Abstract

Abstract:

A mono-nitrophenylamino-β-cyclodextrin was synthesized and bonded to the surface of ordered mesoporous SBA-15 for high performance liquid chromatography(HPLC), which obtained a novel 6-mono-nitrophenylamino-β-cyclodextrin bonded SBA-15 chiral stationary phase(NCDSP). Its structure and morphology were characterized by infrared spectroscopy, elemental analysis, thermal gravimetric analysis, mass spectrometry, scanning electron microscopy, transmission electron microscopy and X-ray diffraction. The basic chromatographic property of new NCDSP was evaluated and used for enantioseparations of chiral drugs such as β-blockers and dihydroflavanones. The fourteen kinds of β-blockers and six kinds of dihydroflavanones chiral drugs can be separated on NCDSP. The resolutions of metoprolol enantiomers and 2'-hydroxy flavanone enantiomers reached 1.75 and 5.21 within 20 min, respectively. By comparative study with PCDSP, some enantio-separation mechanisms of the new stationary phase were also discussed.

Key words: High performance liquid chromatography, β-Cyclodextrin-bonded SBA-15 stationary phase, Chiral separation, β-Blocker, Dihydroflavanone, Chiral drug

CLC Number:

O657

TrendMD:

ZHOU Rendan, LI Laisheng, CHENG Biaoping, NIE Guizhen, ZHANG Hongfu. Preparation and Evaluation of a Novel 6-mono-Nitrophenylamino-β-cyclodextrin Bonded SBA-15 Chiral Stationary Phase for HPLC^†[J]. Chem. J. Chinese Universities, 2014, 35(6): 1152.

Figures/Tables 9

References 20

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Compound	k₁	k₂	k₃	α	R_s	V(ACN)∶V(MeOH)∶V(TEA)∶V(HOAc)	λ/nm
Metoprolol	1.93	2.28		1.18	1.75	95∶5∶2∶2	275
Alprenolol	1.96	2.12		1.08	0.91	95∶5∶1∶1	270
Atenolol	4.07	4.76		1.17	1.56	95∶5∶4∶4	275
Propranolol	2.22	2.59		1.17	1.51	95∶5∶1.5∶1.5	290
Esmolol	1.76	2.11		1.20	1.67	95∶5∶2∶2	275
Pindolol	2.91	3.09		1.06	0.80	97∶3∶2∶2	263
Labetalol	2.36	2.59	2.86			95∶5∶4∶4	306
Nadolol	2.91	3.10	3.46			95∶5∶4∶4	276
Bisoprolol	2.92	3.16		1.08	0.68	95∶5∶1∶1	272
Sotalol	1.66	1.72		1.04	0.85	95∶5∶4∶4	275
Carteolol	2.67	2.84		1.06	0.76	95∶5∶2∶2	254
Celiprolol	1.99	2.10		1.06	0.84	95∶5∶2∶2	332
Arotinolol	2.97	3.41		1.15	1.21	95∶5∶4∶4	316
Carvedilol	2.43	2.84		1.17	1.58	95∶5∶2∶2	285

Compound	k₁	k₂	k₃	α	R_s	V(ACN)∶V(MeOH)∶V(TEA)∶V(HOAc)	λ/nm
Metoprolol	1.93	2.28		1.18	1.75	95∶5∶2∶2	275
Alprenolol	1.96	2.12		1.08	0.91	95∶5∶1∶1	270
Atenolol	4.07	4.76		1.17	1.56	95∶5∶4∶4	275
Propranolol	2.22	2.59		1.17	1.51	95∶5∶1.5∶1.5	290
Esmolol	1.76	2.11		1.20	1.67	95∶5∶2∶2	275
Pindolol	2.91	3.09		1.06	0.80	97∶3∶2∶2	263
Labetalol	2.36	2.59	2.86			95∶5∶4∶4	306
Nadolol	2.91	3.10	3.46			95∶5∶4∶4	276
Bisoprolol	2.92	3.16		1.08	0.68	95∶5∶1∶1	272
Sotalol	1.66	1.72		1.04	0.85	95∶5∶4∶4	275
Carteolol	2.67	2.84		1.06	0.76	95∶5∶2∶2	254
Celiprolol	1.99	2.10		1.06	0.84	95∶5∶2∶2	332
Arotinolol	2.97	3.41		1.15	1.21	95∶5∶4∶4	316
Carvedilol	2.43	2.84		1.17	1.58	95∶5∶2∶2	285

Compound	k₁	k₂	α	R_s	V(1%TEAA)∶V(ACN)	λ/nm
Flavanone	3.97	4.26	1.07	0.69	80∶20	254
6-Methoxy flavanone	3.77	3.95	1.05	0.54	80∶20	256
7-Methoxy flavanone	3.69	3.95	1.07	0.86	80∶20	276
6-Hydroxy flavanone	2.61	2.61	1.00	0.00	80∶20	256
2'-Hydroxy flavanone	2.48	3.23	1.30	3.50	80∶20	254
4'-Hydroxy flavanone	2.91	3.33	1.14	1.63	80∶20	254

Compound	k₁	k₂	α	R_s	V(1%TEAA)∶V(ACN)	λ/nm
Flavanone	3.97	4.26	1.07	0.69	80∶20	254
6-Methoxy flavanone	3.77	3.95	1.05	0.54	80∶20	256
7-Methoxy flavanone	3.69	3.95	1.07	0.86	80∶20	276
6-Hydroxy flavanone	2.61	2.61	1.00	0.00	80∶20	256
2'-Hydroxy flavanone	2.48	3.23	1.30	3.50	80∶20	254
4'-Hydroxy flavanone	2.91	3.33	1.14	1.63	80∶20	254

Compound	k₁	k₂	α	R_s	V(1%TEAA)∶V(MeOH)	λ/nm
Flavanone	4.40	4.64	1.05	0.54	60∶40	254
6-Methoxy flavanone	4.74	5.16	1.09	0.97	60∶40	256
7-Methoxy flavanone	4.87	5.50	1.13	1.56	60∶40	276
6-Hydroxy flavanone	2.78	2.99	1.08	0.85	60∶40	256
2'-Hydroxy flavanone	3.03	4.25	1.40	5.21	60∶40	254
4'-Hydroxy flavanone	3.40	3.40	1.00	0.00	60∶40	254