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

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...

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Detalles Bibliográficos
Autores principales: Feagin, Trevor A., Shah, Nirmal I., Heemstra, Jennifer M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Hindawi Publishing Corporation 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3400375/
https://www.ncbi.nlm.nih.gov/pubmed/22848796
http://dx.doi.org/10.1155/2012/354549
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author Feagin, Trevor A.
Shah, Nirmal I.
Heemstra, Jennifer M.
author_facet Feagin, Trevor A.
Shah, Nirmal I.
Heemstra, Jennifer M.
author_sort Feagin, Trevor A.
collection PubMed
description 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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spelling pubmed-34003752012-07-30 Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone Feagin, Trevor A. Shah, Nirmal I. Heemstra, Jennifer M. J Nucleic Acids Research Article 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. Hindawi Publishing Corporation 2012 2012-07-10 /pmc/articles/PMC3400375/ /pubmed/22848796 http://dx.doi.org/10.1155/2012/354549 Text en Copyright © 2012 Trevor A. Feagin et al. https://creativecommons.org/licenses/by/3.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Feagin, Trevor A.
Shah, Nirmal I.
Heemstra, Jennifer M.
Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone
title Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone
title_full Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone
title_fullStr Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone
title_full_unstemmed Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone
title_short Convenient and Scalable Synthesis of Fmoc-Protected Peptide Nucleic Acid Backbone
title_sort convenient and scalable synthesis of fmoc-protected peptide nucleic acid backbone
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3400375/
https://www.ncbi.nlm.nih.gov/pubmed/22848796
http://dx.doi.org/10.1155/2012/354549
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