Resolution of diastereomers of N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine (quadrol) by reversed-phase high-performance liquid chromatography.

J A Fulton, H K Pokharna, M J Dunphy, D J Smith

Index: J. Chromatogr. A. 455 , 183-92, (1988)

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Abstract

Quadrol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine, has been recently observed to display biological activity. It is an immunostimulant and has been implicated as a potentially useful agent in accelerated wound healing. Quadrol exists as a mixture of four unique diastereomers, each of which may, upon further investigation, display differences in biological activity. This paper describes an high-performance liquid chromatographic procedure (both analytical and prep) for the separation of the Quadrol diastereomers. Gas-liquid chromatography and NMR data are presented which corroborate the high-performance liquid chromatographic results. This procedure may be used to obtain pure Quadrol diastereomers, to monitor the progress of Quadrol synthesis from propylene oxide and ethylenediamine or to develop a quantitative assay for Quadrol diastereomers.