Glycol and olefin electrophoric release tags

Article abstract of DOI:10.1016/S0040-4020(01)87912-6

An "electrophoric release tag" is a molecular labeling reagent which comprises three covalently-connected groups: electrophore/release/ reactivity. This reagent is first covalently attached via its reactivity group to a substance of interest. The subsequent release tag-substance conjugate is detected by chemically cleaving the release group within the release tag, liberating the electrophore for eventual detection by electron capture in the gas phase. Here electrophoric release tags are advanced by the preparation of three similar tags having a glycol release group. One of the glycol tags, N-(pentafluorobenzoyl)-4-piperidylidenyl-acetic acid glycol, is attached to glycine methyl ester as a model analyte. The resulting conjugate is cleaved within 5 minutes by aqueous periodate at room temperature, releasing the electrophore N-(pentafluorobenzoyl)-4-piperidone, for detection. Also a tag with an olefin release group is prepared: m-(pentafluorobenzyloxy)-E-3-methylcinnamoyl chloride. The latter reagent is attached to thymidine as a model analyte and a subsequent methylated conjugate is cleaved within 1 hr by aqueous permanganate/ periodate, releasing the electrophore m-(pentafluorobenzyloxy)-acetophenone for detection.