Ketone electrophores and an olefin-release group electrophore-labeled DNA oligomer Detection via electron capture

Abstract

Sixteen ketone electrophores were synthesized (4′-pentafluorobenzyloxyacetophenone, 1, and fifteen analogs thereof). As intended, each gave a high response by gas chromatography with electron capture detection (GC-ECD) as well as GC with detection by electron capture mass spectrometry (GC-EC-MS). Each spectrum by the latter technique consisted of a single major ion. As a representative compound, 1 was converted to a corresponding olefin, N-hydroxysuccinimide ester, which, in turn, was attached covalently to a DNA oligomer. Detection of the latter species spotted onto a nylon membrane was achieved by the sequence permanganate oxidation (which reformed and thereby released 1), hexane extraction, silica solid phase extraction and GC-EC-MS (giving a peak for 1). These results demonstrate potential for olefin-release group electrophores to function as multiplicity labels in assays involving DNA probes.