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Issue 6, 2005
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Side chain homologation of alanyl peptide nucleic acids: pairing selectivity and stacking

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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.

Graphical abstract: Side chain homologation of alanyl peptide nucleic acids: pairing selectivity and stacking

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Publication details

The article was received on 28 Jul 2004, accepted on 13 Jan 2005 and first published on 14 Feb 2005


Article type: Paper
DOI: 10.1039/B411545G
Org. Biomol. Chem., 2005,3, 1058-1066

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    Side chain homologation of alanyl peptide nucleic acids: pairing selectivity and stacking

    U. Diederichsen, D. Weicherding and N. Diezemann, Org. Biomol. Chem., 2005, 3, 1058
    DOI: 10.1039/B411545G

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