Exploring solvent versatility in immobilized cellulose-based chiral stationary phase for the enantioselective liquid chromatographic resolution of racemates

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Abstract

Chiralpak IB, a new chiral stationary phase (CSP) containing cellulose tris(3,5-dimethylphenylcarabamate) immobilized onto silica gel, is investigated for the direct enantioselective separation of a set of racemic N-alkylated barbiturates and analogs of thalidomide alkylated in position 3 of the piperidin-2,6-dione ring using different nonstandard solvents such as dichloromethane (DCM), ethyl acetate, THF, methyl tert-butyl ether as an eluent and diluent, respectively, in HPLC. The separation, resolution, and elution order of the investigated compounds were compared on both immobilized and coated cellulose tris(3,5-dimethylphenylcarbamate) CSPs (Chiralpak IB and Chiralcel OD, respectively) using a mixture of n-hexane/2-propanol (90:10 v/v) as mobile phase with different flow-rates and fixed UV detection at 254 nm. The effect of the immobilization of the cellulose tris-(3,5-dimethylphenylcarbamate) CSP on silica (Chiralpak IB) on the chiral recognition ability was noted as the coated phase (Chiralcel OD) possesses a higher resolving power in some cases than the immobilized one (Chiralpak IB). However, a few racemates, which were not or poorly resolved on the immobilized Chiralpak IB or the coated Chiralcel OD when using standard solvents were most efficiently resolved on the immobilized Chiralpak IB upon using nonstandard solvents. Furthermore, the immobilized phase withstands the nonstandard (prohibited) HPLC solvents mentioned previously when used as eluents or as a dissolving agent for the analyte itself. An example of inversion or apparent inversion of elution order on Chiralpak IB is reported. The direct analysis of a spiked plasma sample extracted using DCM on Chiralpak IB is also shown.

Original languageEnglish
Pages (from-to)1019-1028
Number of pages10
JournalJournal of Separation Science
Volume30
Issue number7
DOIs
Publication statusPublished - 2007
Externally publishedYes

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Cellulose
Dichloromethane
Liquids
Methylene Chloride
Optical resolving power
Silica gel
Propanol
Hexane
Barbiturates
Thalidomide
2-Propanol
Silica Gel
Ethers
Silicon Dioxide
Silica
Flow rate
Plasmas
cellulose tris-3,5-dimethylphenyl-carbamate

Cite this

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title = "Exploring solvent versatility in immobilized cellulose-based chiral stationary phase for the enantioselective liquid chromatographic resolution of racemates",
abstract = "Chiralpak IB, a new chiral stationary phase (CSP) containing cellulose tris(3,5-dimethylphenylcarabamate) immobilized onto silica gel, is investigated for the direct enantioselective separation of a set of racemic N-alkylated barbiturates and analogs of thalidomide alkylated in position 3 of the piperidin-2,6-dione ring using different nonstandard solvents such as dichloromethane (DCM), ethyl acetate, THF, methyl tert-butyl ether as an eluent and diluent, respectively, in HPLC. The separation, resolution, and elution order of the investigated compounds were compared on both immobilized and coated cellulose tris(3,5-dimethylphenylcarbamate) CSPs (Chiralpak IB and Chiralcel OD, respectively) using a mixture of n-hexane/2-propanol (90:10 v/v) as mobile phase with different flow-rates and fixed UV detection at 254 nm. The effect of the immobilization of the cellulose tris-(3,5-dimethylphenylcarbamate) CSP on silica (Chiralpak IB) on the chiral recognition ability was noted as the coated phase (Chiralcel OD) possesses a higher resolving power in some cases than the immobilized one (Chiralpak IB). However, a few racemates, which were not or poorly resolved on the immobilized Chiralpak IB or the coated Chiralcel OD when using standard solvents were most efficiently resolved on the immobilized Chiralpak IB upon using nonstandard solvents. Furthermore, the immobilized phase withstands the nonstandard (prohibited) HPLC solvents mentioned previously when used as eluents or as a dissolving agent for the analyte itself. An example of inversion or apparent inversion of elution order on Chiralpak IB is reported. The direct analysis of a spiked plasma sample extracted using DCM on Chiralpak IB is also shown.",
keywords = "Cellulose tris (3,5-dimethylphenylcarbamate), Chiralcel OD, Chiralpak IB, Elution order, Enantioseparation, HPLC, N-Alkylated barbiturates, Thalidomide analogs",
author = "Ashraf Ghanem",
year = "2007",
doi = "10.1002/jssc.200600357",
language = "English",
volume = "30",
pages = "1019--1028",
journal = "HRC Journal of High Resolution Chromatography",
issn = "1615-9306",
publisher = "Wiley-VCH Verlag",
number = "7",

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TY - JOUR

T1 - Exploring solvent versatility in immobilized cellulose-based chiral stationary phase for the enantioselective liquid chromatographic resolution of racemates

AU - Ghanem, Ashraf

PY - 2007

Y1 - 2007

N2 - Chiralpak IB, a new chiral stationary phase (CSP) containing cellulose tris(3,5-dimethylphenylcarabamate) immobilized onto silica gel, is investigated for the direct enantioselective separation of a set of racemic N-alkylated barbiturates and analogs of thalidomide alkylated in position 3 of the piperidin-2,6-dione ring using different nonstandard solvents such as dichloromethane (DCM), ethyl acetate, THF, methyl tert-butyl ether as an eluent and diluent, respectively, in HPLC. The separation, resolution, and elution order of the investigated compounds were compared on both immobilized and coated cellulose tris(3,5-dimethylphenylcarbamate) CSPs (Chiralpak IB and Chiralcel OD, respectively) using a mixture of n-hexane/2-propanol (90:10 v/v) as mobile phase with different flow-rates and fixed UV detection at 254 nm. The effect of the immobilization of the cellulose tris-(3,5-dimethylphenylcarbamate) CSP on silica (Chiralpak IB) on the chiral recognition ability was noted as the coated phase (Chiralcel OD) possesses a higher resolving power in some cases than the immobilized one (Chiralpak IB). However, a few racemates, which were not or poorly resolved on the immobilized Chiralpak IB or the coated Chiralcel OD when using standard solvents were most efficiently resolved on the immobilized Chiralpak IB upon using nonstandard solvents. Furthermore, the immobilized phase withstands the nonstandard (prohibited) HPLC solvents mentioned previously when used as eluents or as a dissolving agent for the analyte itself. An example of inversion or apparent inversion of elution order on Chiralpak IB is reported. The direct analysis of a spiked plasma sample extracted using DCM on Chiralpak IB is also shown.

AB - Chiralpak IB, a new chiral stationary phase (CSP) containing cellulose tris(3,5-dimethylphenylcarabamate) immobilized onto silica gel, is investigated for the direct enantioselective separation of a set of racemic N-alkylated barbiturates and analogs of thalidomide alkylated in position 3 of the piperidin-2,6-dione ring using different nonstandard solvents such as dichloromethane (DCM), ethyl acetate, THF, methyl tert-butyl ether as an eluent and diluent, respectively, in HPLC. The separation, resolution, and elution order of the investigated compounds were compared on both immobilized and coated cellulose tris(3,5-dimethylphenylcarbamate) CSPs (Chiralpak IB and Chiralcel OD, respectively) using a mixture of n-hexane/2-propanol (90:10 v/v) as mobile phase with different flow-rates and fixed UV detection at 254 nm. The effect of the immobilization of the cellulose tris-(3,5-dimethylphenylcarbamate) CSP on silica (Chiralpak IB) on the chiral recognition ability was noted as the coated phase (Chiralcel OD) possesses a higher resolving power in some cases than the immobilized one (Chiralpak IB). However, a few racemates, which were not or poorly resolved on the immobilized Chiralpak IB or the coated Chiralcel OD when using standard solvents were most efficiently resolved on the immobilized Chiralpak IB upon using nonstandard solvents. Furthermore, the immobilized phase withstands the nonstandard (prohibited) HPLC solvents mentioned previously when used as eluents or as a dissolving agent for the analyte itself. An example of inversion or apparent inversion of elution order on Chiralpak IB is reported. The direct analysis of a spiked plasma sample extracted using DCM on Chiralpak IB is also shown.

KW - Cellulose tris (3,5-dimethylphenylcarbamate)

KW - Chiralcel OD

KW - Chiralpak IB

KW - Elution order

KW - Enantioseparation

KW - HPLC

KW - N-Alkylated barbiturates

KW - Thalidomide analogs

UR - http://www.scopus.com/inward/record.url?scp=34249680757&partnerID=8YFLogxK

U2 - 10.1002/jssc.200600357

DO - 10.1002/jssc.200600357

M3 - Article

VL - 30

SP - 1019

EP - 1028

JO - HRC Journal of High Resolution Chromatography

JF - HRC Journal of High Resolution Chromatography

SN - 1615-9306

IS - 7

ER -