Literature DB >> 24311449

Mild bioconjugation through the oxidative coupling of ortho-aminophenols and anilines with ferricyanide.

Allie C Obermeyer1, John B Jarman, Chawita Netirojjanakul, Kareem El Muslemany, Matthew B Francis.   

Abstract

Using a small-molecule-based screen, ferricyanide was identified as a mild and efficient oxidant for the coupling of anilines and o-aminophenols on protein substrates. This reaction is compatible with thiols and 1,2-diols, allowing its use in the creation of complex bioconjugates for use in biotechnology and materials applications.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amines; bioconjugation; iron; oxidation; proteins

Mesh：

Substances：

Year:  2013        PMID： 24311449     DOI： 10.1002/anie.201307386

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  Click chemistry in complex mixtures: bioorthogonal bioconjugation.

Authors:  Craig S McKay; M G Finn
Journal:  Chem Biol       Date:  2014-09-18

2.  Direct detection of nitrotyrosine-containing proteins using an aniline-based oxidative coupling strategy.

Authors:  Rapeepat Sangsuwan; Allie C Obermeyer; Phum Tachachartvanich; Krishnan K Palaniappan; Matthew B Francis
Journal:  Chem Commun (Camb)       Date:  2016-07-22       Impact factor: 6.222

3.  Properties of Site-Specifically Incorporated 3-Aminotyrosine in Proteins To Study Redox-Active Tyrosines: Escherichia coli Ribonucleotide Reductase as a Paradigm.

Authors:  Wankyu Lee; Müge Kasanmascheff; Michael Huynh; Anthony Quartararo; Cyrille Costentin; Isabel Bejenke; Daniel G Nocera; Marina Bennati; Cecilia Tommos; JoAnne Stubbe
Journal:  Biochemistry       Date:  2018-04-17       Impact factor: 3.162

4.  An Oxidative Bioconjugation Strategy Targeted to a Genetically Encoded 5-Hydroxytryptophan.

Authors:  Partha Sarathi Addy; James S Italia; Abhishek Chatterjee
Journal:  Chembiochem       Date:  2018-06-01       Impact factor: 3.164

5.  Controlled levels of protein modification through a chromatography-mediated bioconjugation.

Authors:  Richard L Kwant; Jake Jaffe; Peter J Palmere; Matthew B Francis
Journal:  Chem Sci       Date:  2015-02-27       Impact factor: 9.825

Review 6.  ortho-Quinones and Analogues Thereof: Highly Reactive Intermediates for Fast and Selective Biofunctionalization.

Authors:  Jorick J Bruins; Bauke Albada; Floris van Delft
Journal:  Chemistry       Date:  2017-12-19       Impact factor: 5.236
  6 in total

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