B. Falkiewicz et al., Synthesis of achiral and chiral peptide nucleic acid (PNA) monomers using Mitsunobu reaction, TETRAHEDRON, 57(37), 2001, pp. 7909-7917
Peptide nucleic acids (PNAs) are intensively studied DNA analogues. We elab
orated an efficient procedure for the synthesis of N-, C-protected pseudodi
peptides with a reduced peptide bond and then peptide nucleic acid (PNA) mo
nomers, based on the Mitsunobu reaction of N-Boc-beta -amino alcohols with
N-o-nitrobenzenesulfonyl-protected (oNBS-protected) amino acid esters. Usin
g the new procedure, we obtained protected PNA monomer backbones with vario
us amino acid side chains. The pseudodipeptide, secondary amine groups were
then deprotected by thiolysis, and after appropriate work-up, acylated wit
h thymin-1-ylacetic acid to give the protected monomers. The procedure seem
s to be of general applicability and allows various modifications of PNA st
ructure by using diverse alcohols and amino acid esters. (C) 2001 Elsevier
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