Properties of 2,4-dinitrophenyl derivatives of amino acids as analytical forms for high-performance liquid chromatography

Boichenko, Alexander P.; Chernyshova, O. S.; Kulikov, A. Yu.; Loginova, Lidia P.

doi:10.1134/s1070427211060103

Cited by 5 publications

(1 citation statement)

References 24 publications

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“…The identification and separation of AAs are crucial in various important processes such as structural analysis of proteins, medicinal preparations, pharmaceutical assays, and identification of biomarkers in many diseases [22–25]. AAs in their native forms represent a challenge in separation and detection as they have a wide range of polarity differences due to the presence of hydrophobic and hydrophilic side chain groups and weak absorbance of light in the UV/Vis region [26]. The attachment of a dinitrophenyl (DNP) group to the primary aliphatic amine of the AA has been a widely used strategy to increase the UV absorbance ability, π‐π interactions and hydrophobicity due to the presence of substituted aniline and nitro chromophore groups.…”

Section: Resultsmentioning

confidence: 99%

Precursor carboxy‐silica for functionalization with interactive ligands. I. Carbodiimide‐assisted preparation of silica‐bonded stationary phases with octadecyl, naphthyl, and anthracenyl ligands: Comparison of their selectivity and retentivity

Paranamana

Rassi

2020

J of Separation Science

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A precursor carboxy-silica support was introduced for grafting retentive ligands for use in high-performance liquid chromatography. This support was prepared by sequentially reacting 5 μm silica particles with vinyltrimethoxysilane and then thioglycolic acid. The carboxy-silica thus obtained was subsequently functionalized with octadecylamine, 2-naphthylamine, or 2-aminoanthracene by oncolumn reactions via a carbodiimide conjugation reaction. The carbodiimide with its zero-length carboxyl-to-amine coupling ability works by activating the surface carboxyl groups of the precursor support for direct reaction with the primary amines of octadecylamine, 2-naphthylamine, or 2-aminoanthracene via amide bond formation. These reactions series, which are applied for the first time in high-performance liquid chromatography column fabrication, yielded the octadecyl-, naphthyl-, and anthracenyl-silica columns. The three columns were evaluated for their reversed-phase chromatography retention properties with alkylbenzenes, alkylphenyl ketones, nitroalkanes, benzene and toluene derivatives, polyaromatic hydrocarbons, and nitro-substituted amino acids. The naphthyl-and anthracenyl-silica exhibited a good selectivity and efficiency toward most of the aromatic analytes when compared to the octadecyl-silica. Nitro-substituted amino acids containing electron withdrawing groups showed greater selectivity than other analytes on the aromatic-based columns than the C 18 column. This is because of the ability of the π electron system of the analyte to accept electrons from the aromatic-based stationary phase (a Lewis base).

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Section: Resultsmentioning

confidence: 99%