Epimerization of peptide nucleic acids analogs during solid-phase synthesis: optimization of the coupling conditions for increasing the optical purity

R Corradini, S Sforza, A Dossena, G Palla…

Index: Corradini, Roberto; Sforza, Stefano; Dossena, Arnaldo; Palla, Gerardo; Rocchi, Raniero; Filira, Ferdinando; Nastri, Flavia; Marchelli, Rosangela Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 20 p. 2690 - 2696

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Citation Number: 29

Abstract

Peptide nucleic acid (PNA) analogs based on Nα-(thymin-1-ylacetyl) ornithine were previously shown to form triplexes with complementary RNA. In order to obtain optically pure compounds for hybridization experiments, chiral monomers based on D-or L-ornithine, Nδ- Fmoc-Nα-(thymin-1-ylacetyl) ornithine 2 and Nδ-Fmoc-Nα-(uracil-1-ylacetyl) ornithine 3 were synthesized either by a one-step or by a simple three-step procedure starting from ...