Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis

A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid de...

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Detalles Bibliográficos
Autores principales: Al-Warhi, Tarfah I., AL-Hazimi, Hassan M.A., El-Faham, Ayman, Albericio, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259230/
https://www.ncbi.nlm.nih.gov/pubmed/21173725
http://dx.doi.org/10.3390/molecules15129403
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author Al-Warhi, Tarfah I.
AL-Hazimi, Hassan M.A.
El-Faham, Ayman
Albericio, Fernando
author_facet Al-Warhi, Tarfah I.
AL-Hazimi, Hassan M.A.
El-Faham, Ayman
Albericio, Fernando
author_sort Al-Warhi, Tarfah I.
collection PubMed
description A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid derivatives as a major product. The oxyma (ethyl 2-cyano-2-(hydroxyimino)acetate) uronium salt was superior to other uronium salts in terms of racemization, while 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT, 9) gave the best results.
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spelling pubmed-62592302018-12-06 Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis Al-Warhi, Tarfah I. AL-Hazimi, Hassan M.A. El-Faham, Ayman Albericio, Fernando Molecules Article A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid derivatives as a major product. The oxyma (ethyl 2-cyano-2-(hydroxyimino)acetate) uronium salt was superior to other uronium salts in terms of racemization, while 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT, 9) gave the best results. MDPI 2010-12-20 /pmc/articles/PMC6259230/ /pubmed/21173725 http://dx.doi.org/10.3390/molecules15129403 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Al-Warhi, Tarfah I.
AL-Hazimi, Hassan M.A.
El-Faham, Ayman
Albericio, Fernando
Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis
title Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis
title_full Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis
title_fullStr Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis
title_full_unstemmed Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis
title_short Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) Derivatives: Application in Solution Peptide Synthesis
title_sort synthesis of 2-(4,6-dimethoxy-1,3,5-triazin-2-yloxyimino) derivatives: application in solution peptide synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259230/
https://www.ncbi.nlm.nih.gov/pubmed/21173725
http://dx.doi.org/10.3390/molecules15129403
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