title: Nucleophilic trapping nitrilimine generated by photolysis of diaryltetrazole in aqueous phase.
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.
authors.affiliation: Division of Biotechnology and Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, CAS, Dalian 116023, China. zhangyx@dicp.ac.cn.
authors.forename: Yixin
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Division of Biotechnology and Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, CAS, Dalian 116023, China. wujunliu@dicp.ac.cn.
authors.forename: Wujun
authors.initials: W
authors.lastname: Liu
authors.affiliation: Division of Biotechnology and Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, CAS, Dalian 116023, China. zhaozb@dicp.ac.cn.
authors.forename: Zongbao K
authors.initials: ZK
authors.lastname: Zhao
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry; D010782:Photolysis; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D007097:Imines; D010455:Peptides; D013777:Tetrazoles; C045574:1H-tetrazole