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Synthesis of Biologically Active Peptide Nucleic Acid−Peptide Conjugates by Sortase-Mediated Ligation

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Leibniz-Institute of Molecular Pharmacology, Robert-Rössle-Strasse 10, 13125 Berlin, Germany [email protected]
Cite this: J. Org. Chem. 2007, 72, 10, 3909–3912
Publication Date (Web):April 14, 2007
https://doi.org/10.1021/jo062331l
Copyright © 2007 American Chemical Society
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    Abstract

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    Sortase A is a transpeptidase that cleaves at a pentapeptide-motif and subsequently transfers the acyl component to a nucleophile containing N-terminal oligoglycines. We investigate the reaction conditions of the sortase-mediated ligation and demonstrate a useful application by the synthesis of a peptide nucleic acid−cell-penetrating peptide chimera, the reaction equilibrium of which can be shifted in favor of the product by dialyzing out the low molecular weight byproduct. The synthesized conjugate exhibits dose-dependent antisense activity.

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    Sortase expression and purification, solid-phase synthesis and characterization of peptides and PNA, and the splicing correction assay. This material is available free of charge via the Internet at http://pubs.acs.org.

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