Polymeric benzotriazole reagent for the off-line high-performanceliquid chromatographic derivatization of polyamines and related nucleophiles in biological fluids

Chou, T.-Y.; Gao, Chun Xin; Colgan, Stephen T.; Krull, Ira S.; Dorschel, C.; Bidlingmeyer, Brian A.

doi:10.1016/s0021-9673(00)88611-2

Cited by 17 publications

(7 citation statements)

References 23 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: 99%

“…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: 99%

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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“…Benzoyl chloride is particularly advantageous because it implies short derivatization procedure and has a long elution time. A rapid and simple method using benzoyl chloride was originally described by Redmond and Tseng [22]. The derivatization method was improved by dissolving benzoyl chloride in methanol thereby enhancing the reaction with polyamines.…”

Section: Benzoyl Chloride [36]mentioning

confidence: 99%

Derivatizing Reagents for Detection of Organic Compounds By HPLC

Chhanikar

Gupta

Umekar

2021

AJACR

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Derivatization is the process of chemically modifying a compound to develope a new compound which has properties that are suitable for analysis using HPLC. Derivatization improves the detectability of a target analyte by reaction with suitable derivatizing agent. Derivatization reactions are simple chemical modification of substance that make it compatible with the selected separation method or transforms substance with a low UV- absorption into highly sensitive product. Derivatization reactions in liquid chromatography modify the solutes adding a chomophore for easy UV detection or a fluorophore for sensitive fluorescent detection. The chemical structure of the compound remains same and just modifies the specific functional group for reacting compounds to derivative of deviating chemical and physical properties in order to make them detectable. Introduction of certain elements or groups through chemical derivatization may enhance the detector’s response helpful for the elucidation of structure of analytes. In conclusion, the present review describe various derivatization reagents for pre-column and post column derivatization process in HPLC by UV-visible and fluorescence detection are summarized along with reactions and some practical aspects. The commonly used derivatizing reagents in HPLC are 1-fluoro-2, 4-dinitrobenzene, ninhydrine, 4-N-N-dimethylaminoazobenzene-4’-sulfonyl chloride, benzoyl chloride, phenyl isocyanate for UV-visible detection and o-phthalaldehyde, fluorescamine, 1-dimethylaminonapthalene-5-sulfonyl chloride (DNS-Cl), 9-fluorenylmethyl chloroformate (Fmoc-Cl), benzofurans for Fluorescence detection.

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“…It is only within the past 10 years that analytical chemists have been attracted to the possible uses of solid-phase reagents for improved derivatizations related to HPLC. We and others have described the significant advantages possible in using this newer approach to achiral derivatizations in analytical chemistry and HPLC (30)(31)(32)(33)(34)(35)(36)(37).…”

Section: Introductionmentioning

confidence: 99%

Chiral polymeric reagents for off-line and on-line derivatizations of enantiomers in high-performance liquid chromatography with ultraviolet and fluorescence detection: an enantiomer recognition approach

Chou¹,

Gao²,

Grinberg³

et al. 1989

Anal. Chem.

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Optically active and detector-sensitive polymeric reagents have been synthesized, loadings determined, derivatizations/separations/detection optimized, and applications to simple amines and amino alcohols described. Such reagents have been designed to contain different chiral centers, usually amino acids, leashed via an activated ester attachment to an insoluble, structurally rigid, organic polymer backbone. 9-Fluorenylmethyl (FMOC) moieties chemically bonded to the amino acids were used as ultraviolet (UV) and fluorescence (FL) sensitive detector probes to the final diastereomers of enantiomer substrates. Such diastereomers can be readily separated by isocratic or gradient elution normal-phase methods. The kinetics for diastereomer formation have been determined, and final UV/FL responses for known mixtures of enantiomers have been compared to demonstrate overall validity of the method. Minimum detection limits, linearity of calibration plots, dual detector responses, and linear diode array spectra and absorbance ratios have also been demonstrated. In some cases, authentic standards have been prepared to calculate absolute percent derivatizations for specific enantiomer pairs. The overall approach permits, for the very first time, off-line or on-line precolumn derivatization for the formation of diastereomers having unique detector properties. It has been proven that the rates and rate constants for such formations are identical for at least those pairs of enantiomers studied. Separations are base-line or near-base-line, permitting accurate and precise quantitative determinations, by both UV and FL, of enantiomer/optical purity and chemical purity.

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Polymeric benzotriazole reagent for the off-line high-performanceliquid chromatographic derivatization of polyamines and related nucleophiles in biological fluids

Cited by 17 publications

References 23 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

Derivatizing Reagents for Detection of Organic Compounds By HPLC

Chiral polymeric reagents for off-line and on-line derivatizations of enantiomers in high-performance liquid chromatography with ultraviolet and fluorescence detection: an enantiomer recognition approach

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