Literature DB >> 27009873

A simple method for enhancing the bioorthogonality of cyclooctyne reagent.

He Tian1, Thomas P Sakmar2, Thomas Huber1.   

Abstract

The cross-reactivity between some cyclooctynes and thiols limits the bioorthogonality of the strain-promoted azide-alkyne cycloaddition reaction. We show that a low concentration of β-mercaptoethanol significantly reduces the undesirable side reaction between bicyclononyne (BCN) and cysteine and while preserving free cysteines. We site-specifically label a genetically-encoded azido group in the visual photoreceptor rhodopsin to demonstrate the utility of the strategy.

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Year:  2016        PMID： 27009873      PMCID： PMC4824645          DOI： 10.1039/c6cc01321j

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


  20 in total

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Authors:  Elham Behshad; Sara E Parkin; J Martin Bollinger
Journal:  Biochemistry       Date:  2004-09-28       Impact factor: 3.162

2.  Oxidized redox state of glutathione in the endoplasmic reticulum.

Authors:  C Hwang; A J Sinskey; H F Lodish
Journal:  Science       Date:  1992-09-11       Impact factor: 47.728

3.  Expanding the genetic code of Escherichia coli.

Authors:  L Wang; A Brock; B Herberich; P G Schultz
Journal:  Science       Date:  2001-04-20       Impact factor: 47.728

4.  Preventing thiol-yne addition improves the specificity of strain-promoted azide-alkyne cycloaddition.

Authors:  Remon van Geel; Ger J M Pruijn; Floris L van Delft; Wilbert C Boelens
Journal:  Bioconjug Chem       Date:  2012-03-08       Impact factor: 4.774

5.  Bioorthogonal fluorescent labeling of functional G-protein-coupled receptors.

Authors:  He Tian; Saranga Naganathan; Manija A Kazmi; Thue W Schwartz; Thomas P Sakmar; Thomas Huber
Journal:  Chembiochem       Date:  2014-07-18       Impact factor: 3.164

6.  Formation of the meta II photointermediate is accompanied by conformational changes in the cytoplasmic surface of rhodopsin.

Authors:  J F Resek; Z T Farahbakhsh; W L Hubbell; H G Khorana
Journal:  Biochemistry       Date:  1993-11-16       Impact factor: 3.162

7.  Mass spectrometry detection and reduction of disulfide adducts between reducing agents and recombinant proteins with highly reactive cysteines.

Authors:  G E Begg; D W Speicher
Journal:  J Biomol Tech       Date:  1999-03

8.  Cysteine residues 110 and 187 are essential for the formation of correct structure in bovine rhodopsin.

Authors:  S S Karnik; T P Sakmar; H B Chen; H G Khorana
Journal:  Proc Natl Acad Sci U S A       Date:  1988-11       Impact factor: 11.205

9.  An expanded eukaryotic genetic code.

Authors:  Jason W Chin; T Ashton Cropp; J Christopher Anderson; Mridul Mukherji; Zhiwen Zhang; Peter G Schultz
Journal:  Science       Date:  2003-08-15       Impact factor: 47.728

10.  Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells.

Authors:  Jan Dommerholt; Samuel Schmidt; Rinske Temming; Linda J A Hendriks; Floris P J T Rutjes; Jan C M van Hest; Dirk J Lefeber; Peter Friedl; Floris L van Delft
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336
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  9 in total

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2.  'Clickable lectins': bioorthogonal reactive handles facilitate the directed conjugation of lectins in a modular fashion.

Authors:  Felix Tobola; Elise Sylvander; Claudia Gafko; Birgit Wiltschi
Journal:  Interface Focus       Date:  2019-02-15       Impact factor: 3.906

Review 3.  Chemical Probes for Redox Signaling and Oxidative Stress.

Authors:  Masahiro Abo; Eranthie Weerapana
Journal:  Antioxid Redox Signal       Date:  2017-12-22       Impact factor: 8.401

4.  Dual-Reactivity trans-Cyclooctenol Probes for Sulfenylation in Live Cells Enable Temporal Control via Bioorthogonal Quenching.

Authors:  Samuel L Scinto; Oshini Ekanayake; Uthpala Seneviratne; Jessica E Pigga; Samantha J Boyd; Michael T Taylor; Jun Liu; Christopher W Am Ende; Sharon Rozovsky; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2019-07-09       Impact factor: 15.419

5.  Development of a bioorthogonal fluorescence-based assay for assessing drug uptake and delivery in bacteria.

Authors:  Jocelyn M F Ooi; Jessica M Fairhall; Benjamin Spangler; Daniel J W Chong; Brian Y Feng; Allan B Gamble; Sarah Hook
Journal:  RSC Adv       Date:  2022-05-23       Impact factor: 4.036

6.  Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes.

Authors:  Vinayak Gupta; Hanumantharao Paritala; Kate S Carroll
Journal:  Bioconjug Chem       Date:  2016-05-09       Impact factor: 4.774

7.  Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes.

Authors:  Jessica G K O'Brien; Andrew Jemas; Papa Nii Asare-Okai; Christopher W Am Ende; Joseph M Fox
Journal:  Org Lett       Date:  2020-12-01       Impact factor: 6.005

8.  RNA binding activates RIG-I by releasing an autorepressed signaling domain.

Authors:  T H Dickey; B Song; A M Pyle
Journal:  Sci Adv       Date:  2019-10-02       Impact factor: 14.136

9.  Proximity-induced caspase-9 activation on a DNA origami-based synthetic apoptosome.

Authors:  Bas J H M Rosier; Albert J Markvoort; Berta Gumí Audenis; Job A L Roodhuizen; Anniek den Hamer; Luc Brunsveld; Tom F A de Greef
Journal:  Nat Catal       Date:  2020-01-06
  9 in total

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