Literature DB >> 29911239

Orthogonal, dual protein labelling by tandem cycloaddition of strained alkenes and alkynes to ortho-quinones and azides.

Jorick J Bruins1, Daniel Blanco-Ania2, Vincent van der Doef1, Floris L van Delft1, Bauke Albada1.   

Abstract

Reaction of cyclopropanated trans-cyclooctene (cpTCO) with in situ generated ortho-quinone is an efficient tool for bioorthogonal protein conjugation. The (4+2)-cycloaddition of cpTCO with ortho-quinone is significantly faster than its cyclooctyne counterpart (BCN). Orthogonal, tandem cpTCO-quinone and BCN-azide cycloadditions afforded a homogeneous, dual labelled antibody-drug conjugate.

Entities:  

Year:  2018        PMID： 29911239     DOI： 10.1039/c8cc02638f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  12 in total

1.  Site-Selective Antibody Functionalization via Orthogonally Reactive Arginine and Lysine Residues.

Authors:  Dobeen Hwang; Napon Nilchan; Alex R Nanna; Xiaohai Li; Michael D Cameron; William R Roush; HaJeung Park; Christoph Rader
Journal:  Cell Chem Biol       Date:  2019-06-20       Impact factor: 8.116

Review 2.  Activatable Small-Molecule Hydrogen Sulfide Donors.

Authors:  Carolyn M Levinn; Matthew M Cerda; Michael D Pluth
Journal:  Antioxid Redox Signal       Date:  2019-10-29       Impact factor: 8.401

3.  Click Chemistry with Cyclopentadiene.

Authors:  Brian J Levandowski; Ronald T Raines
Journal:  Chem Rev       Date:  2021-03-02       Impact factor: 60.622

4.  Flow Photochemical Syntheses of trans-Cyclooctenes and trans-Cycloheptenes Driven by Metal Complexation.

Authors:  Jessica E Pigga; Joseph M Fox
Journal:  Isr J Chem       Date:  2019-10-10       Impact factor: 3.333

5.  Catalytic Activation of Bioorthogonal Chemistry with Light (CABL) Enables Rapid, Spatiotemporally Controlled Labeling and No-Wash, Subcellular 3D-Patterning in Live Cells Using Long Wavelength Light.

Authors:  Andrew Jemas; Yixin Xie; Jessica E Pigga; Jeffrey L Caplan; Christopher W Am Ende; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2022-01-24       Impact factor: 16.383

6.  Site-Specific and Trigger-Activated Modification of Proteins by Means of Catalytic Hemin/G-quadruplex DNAzyme Nanostructures.

Authors:  Jordi F Keijzer; Bauke Albada
Journal:  Bioconjug Chem       Date:  2020-09-18       Impact factor: 4.774

7.  Non-Genetic Generation of Antibody Conjugates Based on Chemoenzymatic Tyrosine Click Chemistry.

Authors:  Jorick J Bruins; Johannes A M Damen; Marloes A Wijdeven; Lianne P W M Lelieveldt; Floris L van Delft; Bauke Albada
Journal:  Bioconjug Chem       Date:  2021-09-14       Impact factor: 4.774

8.  Enabling In Vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Silicon-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts.

Authors:  Chuanqi Wang; He Zhang; Tao Zhang; Xiaoyu Zou; Hui Wang; Julia E Rosenberger; Raghu Vannam; William S Trout; Jonathan B Grimm; Luke D Lavis; Colin Thorpe; Xinqiao Jia; Zibo Li; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2021-07-12       Impact factor: 16.383

9.  Chemoselectivity of Tertiary Azides in Strain-Promoted Alkyne-Azide Cycloadditions.

Authors:  Dennis Svatunek; Nicole Houszka; Trevor A Hamlin; F Matthias Bickelhaupt; Hannes Mikula
Journal:  Chemistry       Date:  2018-12-06       Impact factor: 5.236

10.  Secondary Orbital Interactions Enhance the Reactivity of Alkynes in Diels-Alder Cycloadditions.

Authors:  Brian J Levandowski; Dennis Svatunek; Barbara Sohr; Hannes Mikula; K N Houk
Journal:  J Am Chem Soc       Date:  2019-01-31       Impact factor: 15.419
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