Open Access

Molecules, volume 19, issue 1, pages 306-315

Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase

Yixin Zhang ^{1, 2}

Wujun Liu ¹

Zongbao Zhao ¹

Division of Biotechnology and Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, CAS, Dalian 116023, China |

University of Chinese Academy of Sciences, 19A Yuquanlu, Beijing 100049, China |

Publication type: Journal Article

Publication date: 2013-12-27

MDPI

Journal: Molecules

scimago Q1

SJR: 0.744

CiteScore: 7.4

Impact factor: 4.2

ISSN: 14203049

DOI: 10.3390/molecules19010306

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PubMed ID: 24378969

Organic Chemistry

Drug Discovery

Physical and Theoretical Chemistry

Pharmaceutical Science

Molecular Medicine

Analytical Chemistry

Chemistry (miscellaneous)

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.

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Publisher

MDPI

Journal

Molecules

scimago Q1

SJR

0.744

CiteScore

7.4

Impact factor

4.2

ISSN

14203049 (Print, Electronic)

Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase

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