Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase

Nitrilimine generated by photolysis of diaryltetrazole in aqueous phase under mild conditions was trapped by nucleophiles including amines and thioalcohols. The representative products were characterized, while products with all 20 natural amino acids and a peptide were observed by MALDI-TOF mass sp...

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Detalles Bibliográficos
Autores principales: Zhang, Yixin, Liu, Wujun, Zhao, Zongbao K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271683/
https://www.ncbi.nlm.nih.gov/pubmed/24378969
http://dx.doi.org/10.3390/molecules19010306
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author Zhang, Yixin
Liu, Wujun
Zhao, Zongbao K.
author_facet Zhang, Yixin
Liu, Wujun
Zhao, Zongbao K.
author_sort Zhang, Yixin
collection PubMed
description Nitrilimine generated by photolysis of diaryltetrazole in aqueous phase under mild conditions was trapped by nucleophiles including amines and thioalcohols. The representative products were characterized, while products with all 20 natural amino acids and a peptide were observed by MALDI-TOF mass spectroscopy. Competitive studies showed that this reaction also occurred in the presence of acrylamide. These results provided new information for understanding the potential side reactions when tetrazole-alkene pairs were used as a bioorthogonal reaction in labeling proteins and related studies in buffered systems.
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spelling pubmed-62716832018-12-20 Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase Zhang, Yixin Liu, Wujun Zhao, Zongbao K. Molecules Communication Nitrilimine generated by photolysis of diaryltetrazole in aqueous phase under mild conditions was trapped by nucleophiles including amines and thioalcohols. The representative products were characterized, while products with all 20 natural amino acids and a peptide were observed by MALDI-TOF mass spectroscopy. Competitive studies showed that this reaction also occurred in the presence of acrylamide. These results provided new information for understanding the potential side reactions when tetrazole-alkene pairs were used as a bioorthogonal reaction in labeling proteins and related studies in buffered systems. MDPI 2013-12-27 /pmc/articles/PMC6271683/ /pubmed/24378969 http://dx.doi.org/10.3390/molecules19010306 Text en © 2013 by the authors. 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 Communication
Zhang, Yixin
Liu, Wujun
Zhao, Zongbao K.
Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase
title Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase
title_full Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase
title_fullStr Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase
title_full_unstemmed Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase
title_short Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase
title_sort nucleophilic trapping nitrilimine generated by photolysis of diaryltetrazole in aqueous phase
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271683/
https://www.ncbi.nlm.nih.gov/pubmed/24378969
http://dx.doi.org/10.3390/molecules19010306
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AT liuwujun nucleophilictrappingnitriliminegeneratedbyphotolysisofdiaryltetrazoleinaqueousphase
AT zhaozongbaok nucleophilictrappingnitriliminegeneratedbyphotolysisofdiaryltetrazoleinaqueousphase

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