Pre-chromatographic derivatization of primary and secondary amines with a polymeric anhydride for improved high-performance liquid chromatographic detection

Chou, T.-Y.; Colgan, Stephen T.; Kao, Diana; Krull, Ira S.; Dorschel, C.; Bidlingmeyer, Brian A.

doi:10.1016/s0021-9673(00)94854-4

Cited by 26 publications

(4 citation statements)

References 16 publications

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“…Many optically active mobile-phase additives have been introduced, often by using ligand-exchange chromatography, at times with an amino acid and copper as the metal (9,10). Immobilized, chiral amino acids have also been used for ligand-exchange resolutions, again with a metal in the mobile phase (11)(12)(13)(14)(15). HPLC solution derivatizations for improved detection of chiral molecules have also been extensively reported and reviewed (16)(17)(18)(19)(20).…”

Section: Characterization Of Synthesized External Standardsmentioning

confidence: 99%

“…Following our earlier results that used a polymeric oacetylsalicyl activated anhydride for improved UV and electrochemical (EC) detection of primary and secondary amines (11) , we have recently described a derivatization scheme for these same nucleophiles that used a polymeric benzotriazole activated ester reagent (12). An application of such polymeric reagent was successful in the determination of polyamines in human urine (13).…”

Section: Introductionmentioning

confidence: 98%

“…Just within the past decade, solid-phase approaches have significantly increased in popularity and usage. A number of reports have appeared describing such approaches in HPLC (8)(9)(10)(11)(12)(13). However, relatively few approaches today routinely incorporate any on-line, precolumn, solid-phase derivatizations for any class of substrates.…”

Section: Introductionmentioning

confidence: 99%

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Polymeric activated ester reagents for off-line and on-line derivatizations of amine nucleophiles in high-performance liquid chromatography with ultraviolet and fluorescence detection

Gao¹,

Chou²,

Krull³

1989

Anal. Chem.

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A novel polymeric activated ester reagent has been developed that improves final detectability and chromatographic performance in high-performance liquid chromatography (HPLC) for virtually all primary and secondary amines or amine analogues. This has involved the synthesis, characterization of final reagent, optimization of derivatization and separation conditions, and determination of analytical figures of merit. The polymeric reagent contained an activated ester linkage to the 9-fluorenyl group, which imparted ultraviolet (UV) and fluorescence (FL) detector properties to the final derivatives. Kinetic studies of these solid-phase (heterogeneous) reactions have been conducted, and specific rate constants were compared with those of the analogous solution reaction for the same substrates. Percent derivatizations have reached 90% and 70% for primary and secondary amines, respectively, under optimized conditions. High reaction reproducibility has been obtained by using the on-line approach, for more than 50 separate injections of the same amine substrate with a single solid-phase reactor. These solid-phase derivatizations have led to detection limits for typical amines in the low-parts-per-billion range. The final, overall methods can provide rapid, automatable, accurate, and precise detection and quantitation of primary/secondary amines and amine-like compounds in real-world sample matrices. As an illustrative example, amphetamine spiked in urine has been derivatized off-line and on-line, with minimum sample preparation, and detected via HPLC-UV/FL with acceptable accuracy and precision.

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Section: Characterization Of Synthesized External Standardsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Polymeric activated ester reagents for off-line and on-line derivatizations of amine nucleophiles in high-performance liquid chromatography with ultraviolet and fluorescence detection

Gao¹,

Chou²,

Krull³

1989

Anal. Chem.

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“…Krull and coworkers have done substantial work on the development of bound reagents for analytical derivatisation and have discussed the important advantages of solid-phase derivatisation reactions in HPLC [13][14][15] These and other serious disadvantages of Krull and co-workers [ derivatisation of amines. One of these reagents [16] is a polymeric anhydride containing the o-acetylsalicyl group as the labelling moiety while the others are based on a 9-fluorenylmethyl tag, with the tag being bound to a polymeric backbone through either a benzotriazole linkage[l71 or through an ester-carbonate linkage [la]. A common disadvantage of these reagents is their instability towards moisture.…”

Section: Introductionmentioning

confidence: 99%

Sodium Benzoxazole-2-Sulfonate: A Derivatisation Reagent for the Analysis of Amines and Amino Acids by HPLC With Fluorescence or UV Detection

Idowu

Adewuyi

1993

Journal of Liquid Chromatography

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A mixed‐bed, multi‐derivatization approach using polymeric reagents for derivatizations of amines in high performance liquid chromatographic detection

Gao

Schmalzing

Krull

1991

Biomedical Chromatography

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Immobilized, polymeric reagents containing covalently attached tagging groups have been synthesized and reacted individually, off-line or on-line, pre-column in high performance liquid chromatographic (HPLC) detection. These reagents have also been combined into a single, mixed-bed reactor, useful for simultaneously preparing several derivatives from a single analyte, all at the same time. Each derivative possesses different chromatographic and detection properties, dependent on the nature of the original polymeric reagent containing the immobilized, tagging species. These particular reagents were designed to impart Ultraviolet/fluorescence, Ultraviolet/electrochemistry (oxidative/reductive or oxidative-hv-electrochemistry) to the final derivatives. Variations in the amounts/ratios of polymeric reagents contained in a single mixed-bed reactor will lead to varying ratios of the final derivatives. These can be predicted knowing the approximate reactivity of each polymeric reagent, percent derivatizations, and overall rates for each reagent towards a given substrate. In this first example of mixed-bed, polymeric reagents for improved derivatization approaches in chromatography, emphasis has been placed on simple amines or amine-like analytes. Multiple derivatives can be effectively used to improve the identification of an unknown analyte in a complex sample matrix, as well as to improve the detectability of that analyte. As one real world application, amphetamine in human urine was quantitated via on-line derivatizations with a mixed-bed reactor. With the least sampling work-up, the resulting sample solutions were directly injected into the on-line derivatization HPLC system for quantitation. The method was validated by single blind spiking experiments. The precision and accuracy were acceptable.

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Pre-chromatographic derivatization of primary and secondary amines with a polymeric anhydride for improved high-performance liquid chromatographic detection

Cited by 26 publications

References 16 publications

Polymeric activated ester reagents for off-line and on-line derivatizations of amine nucleophiles in high-performance liquid chromatography with ultraviolet and fluorescence detection

Polymeric activated ester reagents for off-line and on-line derivatizations of amine nucleophiles in high-performance liquid chromatography with ultraviolet and fluorescence detection

Sodium Benzoxazole-2-Sulfonate: A Derivatisation Reagent for the Analysis of Amines and Amino Acids by HPLC With Fluorescence or UV Detection

A mixed‐bed, multi‐derivatization approach using polymeric reagents for derivatizations of amines in high performance liquid chromatographic detection

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