On‐column chiral derivatization of D‐ and L‐amino acids in micellar electrokinetic chromatography by zone mixing

Tivesten, Anna; Örnskov, Eivor; Folestad, Staffan

doi:10.1002/jhrc.1240190414

Cited by 24 publications

(17 citation statements)

References 12 publications

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“…8A and 8B were made at a pressure as low as 12 mbar. In this way we obtained a precision which is in the same order as in our previous work [16]. For retention times there are no significant differences in the precision between pre-and on-column derivatization whereas the relative standard deviation of peak areas is biased by injection of consecutive plugs, three instead of one (typically, RSD = 7-10 O/O>.…”

Section: On-column Derivatizationmentioning

confidence: 68%

Chiral o‐phthaldialdehyde reagents for fluorogenic on‐column labeling of D‐ and L‐amino acids in micellar electrokinetic chromatography

Tivesten

Folestad

1997

Electrophoresis

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Following a recent communication from this laboratory (A. Tivesten et al., J. High Resol. Chromatogr. 1996, 19, 229-233) where on-column chiral derivatization of D- and L-amino acids in micellar electrokinetic chromatography (MEKC) was demonstrated for the first time, we now present further details of the labeling procedure. The basis of the method is the consecutive injection of a sample and the reagent onto the capillary as two discrete plugs. By utilizing their difference in mobility, the zones are mixed by the electrophoretic process in a controllable way. In this way the amino acids are both derivatized within a few seconds and subsequently separated in a single step. Compared with pre-column derivatization, dilution of the original sample is minimized, which is why the method is highly useful for microchemical analytical work, i.e., labeling of nano- to picoliter samples. Four different chiral thiols were compared in this study, 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose (TATG), N-acetyl-L-cysteine (AC), N-acetyl-D-penicillamine (AP), and N-isobutyryl-L-cysteine (IBC). Together with o-phthaldialdehyde (OPA) these constitute the chiral reagent. The reaction rate as well as the spectroscopic and chromatographic properties of the formed derivatives were examined. It was found that the fastest reaction is obtained with OPA/TATG, as was the case with L-alanine (L-ala), and that the rate is greatly affected by the presence and concentration of acetonitrile or methanol. Moreover, OPA/TATG yields superior resolution of D- and L-amino acids over the other OPA/thiol combinations in a sodium dodecyl sulfate (SDS) micellar buffer, whereas the OPA/AC and OPA/IBC-amino acid derivatives have a higher fluorescence quantum yield. With laser-induced fluorescence detection (He-Cd, 325 nm) the mass limit of detection is at the low amol level.

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Section: On-column Derivatizationmentioning

confidence: 68%

Chiral o‐phthaldialdehyde reagents for fluorogenic on‐column labeling of D‐ and L‐amino acids in micellar electrokinetic chromatography

Tivesten

Folestad

1997

Electrophoresis

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“…The diastereomers of racemic amino drugs were resolved by either micellar electrokinetic chromatography (MEKC) or b-CD-MEKC using sodium dodecyl sulfate (SDS) as surfactant. Tivesten et al (1996) reported chiral separation of DL-amino acids after on-column derivatization with OPA and N-acetyl-D-PenA, as CDR. The resulting diastereomers were then successfully resolved by micellar electrokinetc chromatography, enabling the derivatization of samples in the picoliter range.…”

Section: Application Of Pena As Chiral Selector As Cdrmentioning

confidence: 99%

Enantioresolution of dl‐penicillamine

Bhushan

Kumar

2009

Biomedical Chromatography

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Penicillamine (PenA) is a nonproteinogenic amino acid containing a thiol group. The three functional groups in penicillamine undergo characteristic chemical reactions and differ in their ability to participate in various chemical and biochemical reactions. d-penicillamine is more active pharmacologically, while the l-isomer occurs 'naturally'. This review deals with the enantioresolution of PenA both by direct and indirect methods using liquid chromatography. HPLC separation of its diastereomers prepared with different chiral derivatizing reagents (on reversed-phase columns) and separation of the derivatives prepared with achiral reagents (on chiral columns or via ligand exchange mode) has been discussed. Separation of enantiomers tagged with achiral reagent (to add a chromophore for ehanced detection) when there is no diastereomer formation has been considered separately. In addition, application of PenA and its derivatives as chiral selector for enentioresolution of certain other compounds has also been discussed.

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“…With few exceptions, the resolution for all pairs of enantiomers was higher than 3.0. In a couple of reports, Tivesten and Folestad [74,75] have described in details the MEKC separation of D-and L-amino acids after on-column derivatization with a chiral agent. The basis of their method is the consecutive injection of sample and reagent, as two discrete plugs, onto the capillary.…”

Section: Use Of Sds With the Addition Of A Chiral Selectormentioning

confidence: 99%

Determination of amino acids by micellar EKC: Recent advances in method development and novel applications to different matrices

et al. 2007

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The extensive use of CE for the analysis of amino acids has been well documented in a series of research articles and reviews. Aim of this report is to address the attention of the reader on the recent advances of micellar electrokinetic chromatography for the separation and determination of these analytes. Enhancements in selectivity of this technique through the use of pseudostationary phases containing mixed micelles, polymers, and chiral selectors are presented. Selected applications concerning separation and quantitation of even minute amounts of amino acids in: (i) biological fluids; (ii) microdialysates; (iii) plant cells; (iv) food stuff; and (v) pharmaceutical formulations have also been covered. Advantages of MEKC over other techniques for the amino acid analysis have been underlined.

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On‐column chiral derivatization of D‐ and L‐amino acids in micellar electrokinetic chromatography by zone mixing

Cited by 24 publications

References 12 publications

Chiral o‐phthaldialdehyde reagents for fluorogenic on‐column labeling of D‐ and L‐amino acids in micellar electrokinetic chromatography

Chiral o‐phthaldialdehyde reagents for fluorogenic on‐column labeling of D‐ and L‐amino acids in micellar electrokinetic chromatography

Enantioresolution of dl‐penicillamine

Determination of amino acids by micellar EKC: Recent advances in method development and novel applications to different matrices

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