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Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone

Authors
Journal
Journal of Nucleic Acids
2090-0201
Publisher
Hindawi Publishing Corporation
Publication Date
Volume
2012
Identifiers
DOI: 10.1155/2012/354549
Keywords
  • Research Article
Disciplines
  • Chemistry

Abstract

The peptide nucleic acid backbone Fmoc-AEG-OBn has been synthesized via a scalable and cost-effective route. Ethylenediamine is mono-Boc protected, then alkylated with benzyl bromoacetate. The Boc group is removed and replaced with an Fmoc group. The synthesis was performed starting with 50 g of Boc anhydride to give 31 g of product in 32% overall yield. The Fmoc-protected PNA backbone is a key intermediate in the synthesis of nucleobase-modified PNA monomers. Thus, improved access to this molecule is anticipated to facilitate future investigations into the chemical properties and applications of nucleobase-modified PNA.

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