Application of Mitsunobu reaction to solid-phase peptide nucleic acid (PNA) monomer synthesis |
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Authors: | Falkiewicz Bogdan |
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Affiliation: | Faculty of Chemistry, University of Gdańsk, Poland. bogdan_falkiewicz@go2.pl |
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Abstract: | PNA type I monomer backbone with a reduced peptide bond was synthesized on a Merrifield resin in Mitsunobu reaction of Boc-aminoethanol with resin-bound o-nitrobenzenesulfonylglycine. The pseudodipeptide secondary amine group was deprotected by thiolysis and acylated with thymin-1-ylacetic acid. The monomer was released as a methyl ester. The procedure seems to be of general applicability and allows various modifications of PNA structure by using diverse alcohols and amino acid esters. |
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