1-Methoxycarbonylindolizine-3,5-dicarbaldehyde as a derivatization reagent for amino compounds in high-performance capillary electrophoresis

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Abstract
The indolizine derivative 1-methoxycarbonylindolizine-3,5-dicarbaldehyde (IDA) was synthesized from 2-(1,3-dioxolan-2-yl)pyridine in four steps. The reactivity of the reagent towards primary amines was investigated by using alanine (Ala) as a model compound. The reagent easily reacted with Ala in 20 mmol l–1 phosphate–borate buffer at pH 10 containing 25–50% v/v of ethanol in the dark at room temperature, and the reaction was completed within 15 min. The IDA derivative of alanine (IDA-Ala) showed a strong absorption at 280 nm (ε= 3.31 × 104 l mol–1 cm–1) and 409 nm (ε= 2.18 × 104 l mol–1 cm–1). The derivative also showed fluorescence at 482 nm when irradiated at 282 or 414 nm. These wavelengths did not overlap with those of IDA. IDA-Ala showed a 1.5 times stronger absorption than that produced by the ninhydrin method, and the fluorescence intensity of IDA-Ala was about three times that produced by o-phthalaldehyde-Ala. On analysis of IDA-Ala by high-performance capillary electrophoresis (HPCE) in the capillary zone electrophoresis (CZE) mode with detection at 280 nm, the calibration graph showed good linearity over the range 0.0172–21.5 µmol ml–1 of alanine. The detection limit for alanine was about 5 nmol ml–1. The relative standard deviations in the determination of IDA-Ala at 10.8 and 21.5 µmol ml–1 were less than 2%(n= 5). Application to the analysis of a mixture of amino acids by HPCE using the micellar electrokinetic chromatography mode is also described.

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