Fast alkene functionalization in vivo by photoclick chemistry: HOMO lifting of nitrile imine dipoles

Yizhong Wang; Wenjiao Song; Wen J. Hu; Qing Lin

doi:10.1002/anie.200901220

Fast alkene functionalization in vivo by photoclick chemistry: HOMO lifting of nitrile imine dipoles

Yizhong Wang
, Wenjiao Song
, Wen J. Hu
, Qing Lin

Chemistry

SUNY Buffalo

Research output: Contribution to journal › Article › peer-review

186 Scopus citations

Abstract

Extremely fast fluorescence labeling (<1 min) of a recombinant alkene-encoded protein in living Escherichia coli cells was observed with tetrazole 1. The electrondonating methoxy substituent raises the energy of the highest occupied molecular orbital of the nitrile-imine intermediate derived from 1. This strategy greatly accelerates the functionalization of alkenes by 1,3-dipolar cycloaddition in living systems.

Original language	English
Pages (from-to)	5330-5333
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	29
DOIs	https://doi.org/10.1002/anie.200901220
State	Published - Jul 6 2009

Keywords

Alkenes
Biotechnology
Dipolar cycloaddition
Frontier-orbital energies
Proteins

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10.1002/anie.200901220

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title = "Fast alkene functionalization in vivo by photoclick chemistry: HOMO lifting of nitrile imine dipoles",

abstract = "Extremely fast fluorescence labeling (<1 min) of a recombinant alkene-encoded protein in living Escherichia coli cells was observed with tetrazole 1. The electrondonating methoxy substituent raises the energy of the highest occupied molecular orbital of the nitrile-imine intermediate derived from 1. This strategy greatly accelerates the functionalization of alkenes by 1,3-dipolar cycloaddition in living systems.",

keywords = "Alkenes, Biotechnology, Dipolar cycloaddition, Frontier-orbital energies, Proteins",

author = "Yizhong Wang and Wenjiao Song and Hu, \{Wen J.\} and Qing Lin",

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T1 - Fast alkene functionalization in vivo by photoclick chemistry

T2 - HOMO lifting of nitrile imine dipoles

AU - Wang, Yizhong

AU - Song, Wenjiao

AU - Hu, Wen J.

AU - Lin, Qing

PY - 2009/7/6

Y1 - 2009/7/6

N2 - Extremely fast fluorescence labeling (<1 min) of a recombinant alkene-encoded protein in living Escherichia coli cells was observed with tetrazole 1. The electrondonating methoxy substituent raises the energy of the highest occupied molecular orbital of the nitrile-imine intermediate derived from 1. This strategy greatly accelerates the functionalization of alkenes by 1,3-dipolar cycloaddition in living systems.

AB - Extremely fast fluorescence labeling (<1 min) of a recombinant alkene-encoded protein in living Escherichia coli cells was observed with tetrazole 1. The electrondonating methoxy substituent raises the energy of the highest occupied molecular orbital of the nitrile-imine intermediate derived from 1. This strategy greatly accelerates the functionalization of alkenes by 1,3-dipolar cycloaddition in living systems.

KW - Alkenes

KW - Biotechnology

KW - Dipolar cycloaddition

KW - Frontier-orbital energies

KW - Proteins

UR - https://www.scopus.com/pages/publications/70349786296

U2 - 10.1002/anie.200901220

DO - 10.1002/anie.200901220

M3 - Article

C2 - 19544336

AN - SCOPUS:70349786296

SN - 1433-7851

VL - 48

SP - 5330

EP - 5333

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 29

ER -

Fast alkene functionalization in vivo by photoclick chemistry: HOMO lifting of nitrile imine dipoles

Abstract

Keywords

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