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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Hindawi Publishing Corporation
2012
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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. |
format | Online Article Text |
id | pubmed-3400375 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Hindawi Publishing Corporation |
record_format | MEDLINE/PubMed |
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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