Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase

被引：34
作者：
Zhang, Yixin [1 ,2 ,3 ]
Liu, Wujun [1 ,2 ]
Zhao, Zongbao K. [1 ,2 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Div Biotechnol, Dalian 116023, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
MOLECULES | 2014年 / 19卷 / 01期
关键词：
photolysis; tetrazole; nucleophilic addition; aqueous-phase reaction; nitrilimine; bioorthogonal reaction; 1,3-DIPOLAR; PHOTOCHEMISTRY; CYCLOADDITIONS; DERIVATIVES; TETRAZOLES; CHEMISTRY; PROTEINS; IMINES;
D O I：
10.3390/molecules19010306
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
引用
收藏
页码：306 / 315
页数：10
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