Specific labelling of sulfhydryl-containing biomolecules with redox-active N-(ferrocenyl)iodoacetamide

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)22_Publication in policy or professional journal

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Original languageEnglish
Pages (from-to)1753-1756
Journal / PublicationJournal of the Chemical Society, Dalton Transactions
Issue number8
Publication statusPublished - 2002


The synthesis, characterisation, X-ray crystal structure and electrochemical properties of a new redox-active labelling reagent, N-(ferrocenyl)iodoacetamide (Fc-IAA), are reported. This compound exhibits a reversible ferrocenium/ferrocene couple at ca. +0.345 V vs. SCE at a sweep rate of 100 mV s-1 in CH3CN at 298 K, and two irreversible reduction waves at ca. -1.324 and -2.048 V, attributable to the reduction of the iodoacetamide group. Since the iodoacetamide moiety can react specifically with the sulfhydryl group, Fc-IAA has been coupled to various biomolecules including a sulfhydryl-modified oligonucleotide, cysteine, glutathione and sulfhydryl-modified bovine serum albumin. The electrochemical properties of the bioconjugates have also been investigated.