Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone. (10th July 2012)

• Record Type: Journal Article
• Authors: Feagin, Trevor A.; Shah, Nirmal I.; Heemstra, Jennifer M.
• Other Names: Bag Subhendu Sekhar Academic Editor.
• Is Part Of: Journal of nucleic acids. Volume 2012(2012)
• Publication Date: 2012-07-10
• Subjects: Nucleic acids -- Periodicals; 572.805
• DOI: 10.1155/2012/354549
• Languages: English
• ISSNs: 2090-0201

Abstract

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.