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

Trevor Feagin | Zendy; Nirmal I. Shah | Zendy; Jennifer M. Heemstra | Zendy

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

Author(s) -

Trevor Feagin,

Nirmal I. Shah,

Jennifer M. Heemstra

Publication year - 2012

Publication title -

journal of nucleic acids

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.621

H-Index - 32

eISSN - 2090-021X

pISSN - 2090-0201

DOI - 10.1155/2012/354549

Subject(s) - nucleobase , peptide nucleic acid , nucleic acid , monomer , combinatorial chemistry , chemistry , protecting group , ethylenediamine , alkylation , peptide , dna , organic chemistry , biochemistry , polymer , catalysis , alkyl

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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