A synthetic strategy for the production of polyfunctional PNAs bearing substituent groups both on the nucleobase and on the backbone C5 carbon of the same monomer is described; this is based on the use of a tris-orthogonally protected monomer and subsequent solid-phase selective functionalization. This strategy can be used for synthesizing PNAs that are not readily accessible by use of preformed modified monomers. As an example, a PNA-based probe that undergoes a switch in its fluorescence emission upon hybridization with a target oligonucleotide, induced by tailor-made movement of two pyrene substituent groups, was synthesized.

A Bifunctional Monomer for On-Resin Synthesis of Polyfunctional PNAs and Tailored Induced-Fit Switching Probes / Manicardi, Alex; Bertucci, Alessandro; Rozzi, Andrea; Corradini, Roberto. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 18:21(2016), pp. 5452-5455. [10.1021/acs.orglett.6b02363]

A Bifunctional Monomer for On-Resin Synthesis of Polyfunctional PNAs and Tailored Induced-Fit Switching Probes

MANICARDI, Alex;BERTUCCI, Alessandro;ROZZI, ANDREA;CORRADINI, Roberto
2016

Abstract

A synthetic strategy for the production of polyfunctional PNAs bearing substituent groups both on the nucleobase and on the backbone C5 carbon of the same monomer is described; this is based on the use of a tris-orthogonally protected monomer and subsequent solid-phase selective functionalization. This strategy can be used for synthesizing PNAs that are not readily accessible by use of preformed modified monomers. As an example, a PNA-based probe that undergoes a switch in its fluorescence emission upon hybridization with a target oligonucleotide, induced by tailor-made movement of two pyrene substituent groups, was synthesized.
A Bifunctional Monomer for On-Resin Synthesis of Polyfunctional PNAs and Tailored Induced-Fit Switching Probes / Manicardi, Alex; Bertucci, Alessandro; Rozzi, Andrea; Corradini, Roberto. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 18:21(2016), pp. 5452-5455. [10.1021/acs.orglett.6b02363]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2820273
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