Convenient and scalable synthesis of Fmoc-protected peptide nucleic acid backbone

Trevor A. Feagin, Nirmal I. Shah, Jennifer M. Heemstra

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


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.

Original languageEnglish
Article number354549
JournalJournal of Nucleic Acids
StatePublished - 2012


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