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Full-Text Articles in Physical Sciences and Mathematics
Effect Of Temperature On Retention Of Enantiomers Of Β-Methyl Amino Acids On A Teicoplanin Chiral Stationary Phase, Antal Péter, Gabriella Török, Daniel W. Armstrong, Géza Tóth, Dirk Tourwé
Effect Of Temperature On Retention Of Enantiomers Of Β-Methyl Amino Acids On A Teicoplanin Chiral Stationary Phase, Antal Péter, Gabriella Török, Daniel W. Armstrong, Géza Tóth, Dirk Tourwé
Chemistry Faculty Research & Creative Works
The isocratic retention of enantiomers of β-methyl amino acids (β-methyltyrosine, β-methylphenylalanine, β-methyltryptophan and β-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) was studied on a teicoplanin-containing chiral stationary phase at different temperatures and at different mobile phase compositions, using the reversed-phase mode. With variation of both mobile phase composition and temperature, almost baseline separations could be achieved for all four enantiomers of sterically hindered amino acids. The retention factors and selectivity factors for the enantiomers of all investigated compounds decreased with increasing temperature. The natural logarithms of the retention factors (ln k) of the investigated compounds depended linearly on the inverse of temperature (1/T). van 't …
High-Performance Liquid Chromatographic Separation Of Enantiomers Of Unusual Amino Acids On A Teicoplanin Chiral Stationary Phase, Antal Péter, Gabriella Török, Daniel W. Armstrong
High-Performance Liquid Chromatographic Separation Of Enantiomers Of Unusual Amino Acids On A Teicoplanin Chiral Stationary Phase, Antal Péter, Gabriella Török, Daniel W. Armstrong
Chemistry Faculty Research & Creative Works
A glycopeptide antibiotic, teicoplanin, was used as chiral stationary phase for the high-performance liquid chromatographic (HPLC) separation of enantiomers of more than 30 unnatural amino acids, such as phenylalanine and tyrosine analogues and analogues containing 1,2,3,4-tetrahydroisoquinoline, tetraline, 1,2,3,4-tetrahydro-2-carboline, cyclopentane, cyclohexane, cyclohexene, bicyclo[2.2.1]heptane or heptene skeletons. Excellent resolutions were achieved for most of the investigated compounds by using a hydro-organic mobile-phase system. The effects of organic modifier content, temperature and flow-rate on the resolution were investigated and the conditions of separation were optimized.
Chiral Separations Of Indan, Tetralin And Benzosuberan Derivatives By Capillary Electrophoresis, Kyung Hyun Gahm, Jauh Tzuoh Lee, Lisa W. Chang, Daniel W. Armstrong
Chiral Separations Of Indan, Tetralin And Benzosuberan Derivatives By Capillary Electrophoresis, Kyung Hyun Gahm, Jauh Tzuoh Lee, Lisa W. Chang, Daniel W. Armstrong
Chemistry Faculty Research & Creative Works
Several indan, tetralin and benzosuberan derivatives of diverse polarities were enantio-resolved by the use of sulfated β-cyclodextrins (CDs) or mixtures of sulfated β-CDs and γ-CD as chiral additives in capillary electrophoresis. Mixtures of sulfated 13-CDs and hydroxypropy1 β- CDs were also successfully utilized for enantiomeric and diastereomeric separations of some of the tetralin derivatives with two stereogenic centers. Both neutral and anionic analytes were resolved in the reversed electrophoretic polarity mode. Cationic amino derivatives of indan and tetralin were enantio-resolved in the conventional electrophoretic polarity mode.
Mechanism Of Capillary Electrophoresis Enantioseparations Using A Combination Of An Achiral Crown Ether Plus Cyclodextrins, Daniel W. Armstrong, L. W. Chang, S. S.C. Chang
Mechanism Of Capillary Electrophoresis Enantioseparations Using A Combination Of An Achiral Crown Ether Plus Cyclodextrins, Daniel W. Armstrong, L. W. Chang, S. S.C. Chang
Chemistry Faculty Research & Creative Works
The addition of an achiral crown ether (18-crown-6) to a cyclodextrin- based separation can significantly affect the capillary electrophoresis (CE) enantioresolution of organic racemates that contain a primary amine functional group. In most cases an enhancement of the enantioseparation was observed. However, there are also cases where the addition of 18-crown-6 was detrimental to a cyclodextrin-based CE enantioseparation. The effect of concentration of the two complexing additives as well as the effect of pH and added potassium ion were examined. A specific three-body complex involving simultaneous, dual inclusion complex formation can be used to explain both the enhanced and diminished …
Chiral Separation Of Monoterpenes Using Mixtures Of Sulfated Β-Cyclodextrins And Α-Cyclodextrin As Chiral Additives In The Reversed-Polarity Capillary Electrophoresis Mode, Kyung Hyun Gahm, Lisa W. Chang, Daniel W. Armstrong
Chiral Separation Of Monoterpenes Using Mixtures Of Sulfated Β-Cyclodextrins And Α-Cyclodextrin As Chiral Additives In The Reversed-Polarity Capillary Electrophoresis Mode, Kyung Hyun Gahm, Lisa W. Chang, Daniel W. Armstrong
Chemistry Faculty Research & Creative Works
The use of mixtures of sulfated β-cyclodextrins and native α-cyclodextrin as chiral additives in capillary electrophoresis was evaluated for the chiral resolution of neutral, cyclic and bicyclic monoterpenes, including α-pinene, (β-pinene, camphene and limonene. Binding properties of sulfated β-cyclodextrins towards these monoterpenes were studied. It was found that there was no enantioresolution of these terpenoids over the concentration range studied. However, the addition of α-cyclodextrin to the running electrolyte in addition to 6.5 mM sulfated β-cyclodextrins, imparted differences in the mobilities of the terpenoid enantiomers and resulted in remarkable enantiomeric separations of α-pinene (R(s)=25), β-pinene (R(s)=12), camphene (R(s)=12) and limonene …
Investigation On Enantiomeric Separations Of Fluorenylmethoxycarbonyl Amino Acids And Peptides By High-Performance Liquid Chromatography Using Native Cyclodextrins As Chiral Stationary Phases, Y. Tang, J. Zukowski, Daniel W. Armstrong
Investigation On Enantiomeric Separations Of Fluorenylmethoxycarbonyl Amino Acids And Peptides By High-Performance Liquid Chromatography Using Native Cyclodextrins As Chiral Stationary Phases, Y. Tang, J. Zukowski, Daniel W. Armstrong
Chemistry Faculty Research & Creative Works
A systematic study was carried out to investigate enantiomeric separations of fluorenylmethoxycarbonyl (FMOC) amino acids and their peptides. Twenty amino acids were derivatized by 9-fluorenylmethyl chloroformate (FMOC-Cl) and its analogues, FMOC-glycyl-Cl and FMOC-β-alanyl-Cl. All derivatives were chromatographed on native β- and γ-cyclodextrin columns using acetonitrile as the main mobile phase component. The results indicated that glycyl and β-alanyl groups between FMOC and amino acid moieties enhanced chiral selectivities of amino acid derivatives. The addition of modifiers, triethylamine, acetic acid and methanol, into the mobile phase caused alterations in retention, enantiorecognition and elution order. The structures of amino acids and the …
Facile Liquid Chromatographic Enantioresolution Of Native Amino Acids And Peptides Using A Teicoplanin Chiral Stationary Phase, Alain Berthod, Youbang Liu, Christina Bagwill, Daniel W. Armstrong
Facile Liquid Chromatographic Enantioresolution Of Native Amino Acids And Peptides Using A Teicoplanin Chiral Stationary Phase, Alain Berthod, Youbang Liu, Christina Bagwill, Daniel W. Armstrong
Chemistry Faculty Research & Creative Works
The glycopeptide antibiotic teicoplanin is shown to be a highly effective stationary phase chiral selector for the resolution of underivatized amino-acid and imino-acid enantiomers. Fifty four of these compounds (including all chiral protein amino acids) as well as a number of dipeptides were resolved. Hydro-organic mobile phases are used and no buffers or added salts are needed in most cases. Hence the purified analytes are easily isolated in pure form, if needed, by evaporating of the solvent. The effect of pH, organic modifier type and amount are discussed. The enantioselective separation mechanism is examined using both molecular modeling and retention …