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
Descripción
Sumario: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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