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A solid-phase CuAAC strategy for the synthesis of PNA containing nucleobase surrogates.

ABSTRACT: The synthesis of an azide containing PNA monomer is described. The monomer was incorporated into two PNA sequences for the purpose of synthesizing an intercalating fluorophore-labeled PNA and a metal binding hairpin using a solid phase copper catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). Click chemistry was performed using 2-ethynylfluorene or 1-ethynylpyrene to add a fluorophore to the PNA, which were tested for their ability to recognize an abasic site on a DNA target. A PNA hairpin possessing azide monomers at each termini was synthesized and reacted with 2-ethynylpyridine to form a hairpin that is stabilized by Ni²?.

SUBMITTER: St Amant AH

PROVIDER: S-EPMC3654728 | biostudies-literature | 2013 Jan-Mar

REPOSITORIES: biostudies-literature

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A solid-phase CuAAC strategy for the synthesis of PNA containing nucleobase surrogates.

St Amant André H AH Engbers Christopher C Hudson Robert H E RH

Artificial DNA, PNA & XNA 20130101 1

The synthesis of an azide containing PNA monomer is described. The monomer was incorporated into two PNA sequences for the purpose of synthesizing an intercalating fluorophore-labeled PNA and a metal binding hairpin using a solid phase copper catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). Click chemistry was performed using 2-ethynylfluorene or 1-ethynylpyrene to add a fluorophore to the PNA, which were tested for their ability to recognize an abasic site on a DNA target. A PNA hairpin po ...[more]

PMID: 23422048

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