A new chiral ferrocene-labelled tyrosine PNA monomer 1 has been synthesised in good yield in both racemic and enantiomerically pure forms. It is suitable for insertion in various positions of PNA oligomers, a possibility that has been preliminarily demonstrated by synthesising the dimer 16. Moreover, in view of possible applications to nucleic acid detection, a preliminary voltammetric investigation on the electrochemical activity of monomer 1 and its synthetic precursors has been carried out in DMF. It appears that, despite the bulkiness of the PNA monomer backbone, its insertion on the ferrocene group only moderately lowers the latter's diffusion coefficients and peak currents, thus affording voltammetric detection limits in the order of 10 -6-10 -7 M.

A new ferrocene conjugate of a tyrosine PNA monomer: synthesis and electrochemical properties / C. Baldoli, L. Falciola, E. Licandro, S. Maiorana, P. Mussini, P. Ramani, C. Rigamonti, G. Zinzalla. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - 689:25(2004), pp. 4791-4802.

A new ferrocene conjugate of a tyrosine PNA monomer: synthesis and electrochemical properties

L. Falciola
Secondo
;
E. Licandro;S. Maiorana;P. Mussini;P. Ramani;C. Rigamonti
Penultimo
;
G. Zinzalla
Ultimo
2004

Abstract

A new chiral ferrocene-labelled tyrosine PNA monomer 1 has been synthesised in good yield in both racemic and enantiomerically pure forms. It is suitable for insertion in various positions of PNA oligomers, a possibility that has been preliminarily demonstrated by synthesising the dimer 16. Moreover, in view of possible applications to nucleic acid detection, a preliminary voltammetric investigation on the electrochemical activity of monomer 1 and its synthetic precursors has been carried out in DMF. It appears that, despite the bulkiness of the PNA monomer backbone, its insertion on the ferrocene group only moderately lowers the latter's diffusion coefficients and peak currents, thus affording voltammetric detection limits in the order of 10 -6-10 -7 M.
Settore CHIM/06 - Chimica Organica
Settore CHIM/01 - Chimica Analitica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/27283
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