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Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis
Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrat...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Hindawi Publishing Corporation
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3133797/ https://www.ncbi.nlm.nih.gov/pubmed/21760822 http://dx.doi.org/10.1155/2011/854952 |
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author | Ramapanicker, Ramesh Gupta, Rohit Megha, Rajendran Chandrasekaran, Srinivasan |
author_facet | Ramapanicker, Ramesh Gupta, Rohit Megha, Rajendran Chandrasekaran, Srinivasan |
author_sort | Ramapanicker, Ramesh |
collection | PubMed |
description | Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrathiomolybdate is exploited to deblock the propargyl esters. The removal of the propargyl group with the neutral reagent tetrathiomolybdate ensures that most of the other protecting groups used in peptide synthesis are untouched. Both acid labile and base labile protecting groups can be removed in the presence of a propargyl ester. Amino acids protected as propargyl esters are employed to synthesize di- to tetrapeptides in solution-phase demonstrating the possible synthetic utilities of the methodology. The methodology described here could be a valuable addition to currently available strategies for peptide synthesis. |
format | Online Article Text |
id | pubmed-3133797 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Hindawi Publishing Corporation |
record_format | MEDLINE/PubMed |
spelling | pubmed-31337972011-07-14 Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis Ramapanicker, Ramesh Gupta, Rohit Megha, Rajendran Chandrasekaran, Srinivasan Int J Pept Research Article Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrathiomolybdate is exploited to deblock the propargyl esters. The removal of the propargyl group with the neutral reagent tetrathiomolybdate ensures that most of the other protecting groups used in peptide synthesis are untouched. Both acid labile and base labile protecting groups can be removed in the presence of a propargyl ester. Amino acids protected as propargyl esters are employed to synthesize di- to tetrapeptides in solution-phase demonstrating the possible synthetic utilities of the methodology. The methodology described here could be a valuable addition to currently available strategies for peptide synthesis. Hindawi Publishing Corporation 2011 2011-06-16 /pmc/articles/PMC3133797/ /pubmed/21760822 http://dx.doi.org/10.1155/2011/854952 Text en Copyright © 2011 Ramesh Ramapanicker 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 Ramapanicker, Ramesh Gupta, Rohit Megha, Rajendran Chandrasekaran, Srinivasan Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis |
title | Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis |
title_full | Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis |
title_fullStr | Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis |
title_full_unstemmed | Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis |
title_short | Applications of Propargyl Esters of Amino Acids in Solution-Phase Peptide Synthesis |
title_sort | applications of propargyl esters of amino acids in solution-phase peptide synthesis |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3133797/ https://www.ncbi.nlm.nih.gov/pubmed/21760822 http://dx.doi.org/10.1155/2011/854952 |
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