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Molecules 2014, 19(1), 306-315; doi:10.3390/molecules19010306
Communication

Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase

1,2
,
1
 and
1,*
1 Division of Biotechnology and Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, CAS, Dalian 116023, China 2 University of Chinese Academy of Sciences, 19A Yuquanlu, Beijing 100049, China
* Author to whom correspondence should be addressed.
Received: 1 October 2013 / Revised: 6 December 2013 / Accepted: 18 December 2013 / Published: 27 December 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

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.
Keywords: photolysis; tetrazole; nucleophilic addition; aqueous-phase reaction; nitrilimine; bioorthogonal reaction photolysis; tetrazole; nucleophilic addition; aqueous-phase reaction; nitrilimine; bioorthogonal reaction
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.

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Zhang, Y.; Liu, W.; Zhao, Z.K. Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase. Molecules 2014, 19, 306-315.

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