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  • Title: Side chain homologation of alanyl peptide nucleic acids: pairing selectivity and stacking.
    Author: Diederichsen U, Weicherding D, Diezemann N.
    Journal: Org Biomol Chem; 2005 Mar 21; 3(6):1058-66. PubMed ID: 15750649.
    Abstract:
    Alanyl peptide nucleic acids (alanyl-PNAs) are oligomers based on a regular peptide backbone with alternating configuration of the amino acids. All side chains are modified by covalently linked nucleobases. Alanyl-PNAs form very rigid, well defined, and linear double strands based on hydrogen bonding of complementary strands, stacking, and solvation. Side chain homology was examined by comparing a methylene linker (alanyl-PNA) with an ethylene linker (homoalanyl-PNA), a trimethylene linker (norvalyl-PNA), and PNA sequences with mixed linker length between nucleobase and backbone. Side chain homology in combination with a linear double strand topology turned out to be valuable in order to selectively manipulate pairing selectivity (pairing mode) and base pair stacking.
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