Modular nucleic acid surrogates. Solid phase synthesis of α-helical peptide nucleic acids (αPNAs)

Abstract

(equation presented) The synthesis and characterization of prototype α-helical peptide nucleic acid (αPNA) modules 1-3 as well as disulfide dimers 4 and 5 are reported. These molecules combine an α-helical peptidyl scaffold with well-defined nucleobase molecular recognition patterns and could serve as a basis for novel antisense and/or antigene agents. Structure assignments for these αPNAs were supported by MALDI-TOF mass spectrometry, and the α-helical nature of 4 in water was confirmed by circular dichroism (CD) spectroscopy.