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An expeditious liquid-phase synthesis of cyclic peptide nucleic acids

✍ Scribed by Jeroen C Verheijen; Gijsbert M Grotenbreg; Ludo Hart de Ruyter; Pieter A.M van der Klein; Gijsbert A van der Marel; Jacques H van Boom

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 129 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00536-0

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✦ Synopsis

Suitably protected linear precursors of cyclic PNAs can be readily obtained by BOP/DiPEA coupling of the corresponding sub-monomers. Conversion of the linear PNA dimers into the pentafluorophenyl esters allows cyclization by intramolecular attack of the deprotected primary amino function under diluted conditions. After removal of the secondary amino protecting group(s), installation of the required nucleobase-acetyl function(s) affords cyclic PNAs. In addition, the latter compounds can be prepared following a direct coupling strategy.

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