Chiral separation of Piperidine-2,6-dione analogues on Chiralpak IA and Chiralpak IB columns using HPLC

Imran Ali, Lahoucine Naim, Ashraf Ghanem, Hassan Aboul-Enein

Research output: Contribution to journalArticle

78 Citations (Scopus)

Abstract

Recently, two new immobilized polysaccharides based CSPs, namely tris-(3,5-dimethylphenylcarbamate) derivatives of amylose and cellulose known as Chiralpak IA and Chiralpak IB were introduced, which may be used with a wide range of solvents including standard and prohibited ones. Several racemic piperidine-2,6-dione analogues [aminoglutethimide, p-nitro-glutethimide, p-nitro-5-aminoglutethimide, cyclohexylaminoglutethimide, phenglutarimide and thalidomide] have been resolved on Chiralpak IA and Chiralpak IB columns (25cmx0.46cm). The non-conventional mobile phases used were methyl-tert-butyl ether-THF (90:10, v/v) [I], 100% dichloromethane [II] and 100% acetonitrile [III] separately at a flow rate of 1.0mL/min using a UV detector at 254nm. The resolution factors for Chiralpak IA and Chiralpak IB columns were 1.00-5.33 and 0.33-0.67, respectively. Chiralpak IA column gave better results than Chiralpak IB column for the reported molecules using the developed HPLC conditions. Experimental conditions and the possible chiral recognition mechanisms have been discussed
Original languageEnglish
Pages (from-to)1013-1017
Number of pages5
JournalTalanta
Volume69
Issue number4
DOIs
Publication statusPublished - 2006
Externally publishedYes

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Aminoglutethimide
Glutethimide
Ultraviolet detectors
Amylose
Thalidomide
Methylene Chloride
Cellulose
Polysaccharides
Flow rate
Derivatives
Molecules
piperidine
methyl tert-butyl ether
phenglutarimide
acetonitrile
cyclohexylaminoglutethimide
Haemophilus influenzae type b-polysaccharide vaccine-diphtheria toxoid conjugate
3,5-dimethylphenylcarbamate

Cite this

Ali, Imran ; Naim, Lahoucine ; Ghanem, Ashraf ; Aboul-Enein, Hassan. / Chiral separation of Piperidine-2,6-dione analogues on Chiralpak IA and Chiralpak IB columns using HPLC. In: Talanta. 2006 ; Vol. 69, No. 4. pp. 1013-1017.
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abstract = "Recently, two new immobilized polysaccharides based CSPs, namely tris-(3,5-dimethylphenylcarbamate) derivatives of amylose and cellulose known as Chiralpak IA and Chiralpak IB were introduced, which may be used with a wide range of solvents including standard and prohibited ones. Several racemic piperidine-2,6-dione analogues [aminoglutethimide, p-nitro-glutethimide, p-nitro-5-aminoglutethimide, cyclohexylaminoglutethimide, phenglutarimide and thalidomide] have been resolved on Chiralpak IA and Chiralpak IB columns (25cmx0.46cm). The non-conventional mobile phases used were methyl-tert-butyl ether-THF (90:10, v/v) [I], 100{\%} dichloromethane [II] and 100{\%} acetonitrile [III] separately at a flow rate of 1.0mL/min using a UV detector at 254nm. The resolution factors for Chiralpak IA and Chiralpak IB columns were 1.00-5.33 and 0.33-0.67, respectively. Chiralpak IA column gave better results than Chiralpak IB column for the reported molecules using the developed HPLC conditions. Experimental conditions and the possible chiral recognition mechanisms have been discussed",
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Chiral separation of Piperidine-2,6-dione analogues on Chiralpak IA and Chiralpak IB columns using HPLC. / Ali, Imran; Naim, Lahoucine; Ghanem, Ashraf; Aboul-Enein, Hassan.

In: Talanta, Vol. 69, No. 4, 2006, p. 1013-1017.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Chiral separation of Piperidine-2,6-dione analogues on Chiralpak IA and Chiralpak IB columns using HPLC

AU - Ali, Imran

AU - Naim, Lahoucine

AU - Ghanem, Ashraf

AU - Aboul-Enein, Hassan

PY - 2006

Y1 - 2006

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AB - Recently, two new immobilized polysaccharides based CSPs, namely tris-(3,5-dimethylphenylcarbamate) derivatives of amylose and cellulose known as Chiralpak IA and Chiralpak IB were introduced, which may be used with a wide range of solvents including standard and prohibited ones. Several racemic piperidine-2,6-dione analogues [aminoglutethimide, p-nitro-glutethimide, p-nitro-5-aminoglutethimide, cyclohexylaminoglutethimide, phenglutarimide and thalidomide] have been resolved on Chiralpak IA and Chiralpak IB columns (25cmx0.46cm). The non-conventional mobile phases used were methyl-tert-butyl ether-THF (90:10, v/v) [I], 100% dichloromethane [II] and 100% acetonitrile [III] separately at a flow rate of 1.0mL/min using a UV detector at 254nm. The resolution factors for Chiralpak IA and Chiralpak IB columns were 1.00-5.33 and 0.33-0.67, respectively. Chiralpak IA column gave better results than Chiralpak IB column for the reported molecules using the developed HPLC conditions. Experimental conditions and the possible chiral recognition mechanisms have been discussed

U2 - 10.1016/j.talanta.2005.12.004

DO - 10.1016/j.talanta.2005.12.004

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JF - Talanta

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