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

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...

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Bibliographic Details
Published in:Journal of Chromatography A 1988, Vol.455, p.183-192
Main Authors: Fulton, J.A., Pokharna, H.K., Dunphy, M.J., Smith, D.J.
Format: Article
Language:English
Subjects:
Analysis
Biological and medical sciences
General pharmacology
Medical sciences
Pharmacology. Drug treatments
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Summary: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.
ISSN:0021-9673
DOI:10.1016/S0021-9673(01)82117-8