Issue 4, 2012
From the journal:

Organic & Biomolecular Chemistry

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

André H. St. Amanta  and  Robert H. E. Hudson*a  

* Corresponding authors

a Department of Chemistry, University of Western Ontario, 1151 Richmond St., London, Canada
E-mail: rhhudson@uwo.ca
Fax: +1-519-661-3022
Tel: +1-519-661-2166

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 T (ΔTm ≥ +6 °C) in a complementary DNA strand. The 2AP monomer showed excellent discrimination of T (ΔTm ≥ +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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Article information

DOI
https://doi.org/10.1039/C1OB06582C
Article type
Paper
Submitted
15 Sep 2011
Accepted
27 Oct 2011
First published
27 Oct 2011

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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