Synthesis of Chirally Pure Ornithine Based PNA Analogues

Alexander C. van der Laan Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA, Leiden, The Netherlands

Irene van Amsterdam Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA, Leiden, The Netherlands

Godefridus I. Tesser Laboratory of Organic Chemistry, Catholic University, Toernooiveld, 6525 ED, Nijmegen, The Netherlands

Jacques H. van Boom Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA, Leiden, The Netherlands

Esther Kuyl‐ Yeheskiel Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA, Leiden, The Netherlands; Karolinska Institute, Department of Medical Biochemistry and Biophysics, S-17177, Stockholm, Sweden

Abstract

A stereoselective synthesis of a chiral PNA analogue containing an ornithine based backbone is described. In this approach each elongation cycle consists of two individual coupling steps: i.e. extension of the free δ-amino function in the growing chain by a TOPPipU mediated coupling with Fmoc-Orn(Boc)-OH, and subsequent acylation of a free α-amine with thymin-1-ylacetic acid. Thyminyl decamers were prepared following this strategy and hybridization experiments indicated that they formed stable complexes with cRNA.

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Synthesis of Chirally Pure Ornithine Based PNA Analogues

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Synthesis of Chirally Pure Ornithine Based PNA Analogues

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