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Issue 4, 2012
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Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine

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Abstract

A Boc-protecting group strategy for Fmoc-based PNA (peptide nucleic acid) oligomerization has been developed for thymine, 2,6-diaminopurine (DAP) and 2-aminopurine (2AP). The monomers may be used interchangeably with standard Fmoc PNA monomers. The DAP monomer was incorporated into a PNA and was found to selectively bind to TTm ≥ +6 °C) in a complementary DNA strand. The 2AP monomer showed excellent discrimination of TTm ≥ +12 °C) over the other nucleobases. 2AP also acted as a fluorescent probe of the PNA:DNA duplexes and displayed fluorescence quenching dependent on the opposite base.

Graphical abstract: Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine

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Publication details

The article was received on 15 Sep 2011, accepted on 27 Oct 2011 and first published on 27 Oct 2011


Article type: Paper
DOI: 10.1039/C1OB06582C
Org. Biomol. Chem., 2012,10, 876-881

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    Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine

    A. H. St. Amant and R. H. E. Hudson, Org. Biomol. Chem., 2012, 10, 876
    DOI: 10.1039/C1OB06582C

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