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 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.
Fulton
J A
JA
Department of Chemistry, University of Akron, OH 44325.
Pokharna
H K
HK
Dunphy
M J
MJ
Smith
D J
DJ
D000276:Adjuvants, Immunologic / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D005029:Ethylenediamines / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000276:Adjuvants, Immunologic; D005029:Ethylenediamines; C010629:1,1',1'',1'''-(ethylenedinitrilo)tetra-2-propanol