The synthesis of new chiral PNA analogues based on lysine is reported. In particular, L- and/or D-lysine-based PNA submonomers bearing two lysine side chains exactly spaced as in the dipeptide Lys-Lys were synthesized and incorporated in the middle of decameric PNA strands, obtaining four diastereomeric (LD, DL, LL and DD) lysine-based chiral PNAs. The hybridization with their complementary antiparallel DNA strand was studied by melting temperature determination and compared with the analogue achiral PNA and chiral PNAs bearing one residue with either of the two lysine enantiomers. The binding abilities were shown to be strongly dependent on the configuration of the stereogenic centres.

Synthesis of new chiral PNAs bearing a dipeptide-mimic monomer with two lysine-derived stereogenic centres / Tedeschi, Tullia; Sforza, Stefano; Corradini, Roberto; Marchelli, Rosangela. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 46:(2005), pp. 8395-8399. [10.1016/j.tetlet.2005.09.157]

Synthesis of new chiral PNAs bearing a dipeptide-mimic monomer with two lysine-derived stereogenic centres

TEDESCHI, Tullia;SFORZA, Stefano;CORRADINI, Roberto;MARCHELLI, Rosangela
2005-01-01

Abstract

The synthesis of new chiral PNA analogues based on lysine is reported. In particular, L- and/or D-lysine-based PNA submonomers bearing two lysine side chains exactly spaced as in the dipeptide Lys-Lys were synthesized and incorporated in the middle of decameric PNA strands, obtaining four diastereomeric (LD, DL, LL and DD) lysine-based chiral PNAs. The hybridization with their complementary antiparallel DNA strand was studied by melting temperature determination and compared with the analogue achiral PNA and chiral PNAs bearing one residue with either of the two lysine enantiomers. The binding abilities were shown to be strongly dependent on the configuration of the stereogenic centres.
2005
Synthesis of new chiral PNAs bearing a dipeptide-mimic monomer with two lysine-derived stereogenic centres / Tedeschi, Tullia; Sforza, Stefano; Corradini, Roberto; Marchelli, Rosangela. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 46:(2005), pp. 8395-8399. [10.1016/j.tetlet.2005.09.157]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/1444545
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