Application of Mitsunobu reaction to solid-phase peptide nucleic acid (PNA) monomer synthesis.
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.
Falkiewicz
Bogdan
B
Faculty of Chemistry, University of Gdańsk, Poland. bogdan_falkiewicz@go2.pl
D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*
D020135:Peptide Nucleic Acids