Literature DB >> 25022431

Strain-promoted cycloadditions involving nitrones and alkynes--rapid tunable reactions for bioorthogonal labeling.

Douglas A MacKenzie1, Allison R Sherratt2, Mariya Chigrinova1, Lawrence L W Cheung1, John Paul Pezacki3.   

Abstract

The development and applications of strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions have brought about new tools for rapid and specific functionalization of biomolecules in different settings. While a number of strain-promoted reactions have been successfully developed, SPANC reactions offer high reactivity with bimolecular rate constants of k2 that are as fast as 60M(-1)s(-1). SPANC reactions also offer stability of starting materials, particularly in the case of endocyclic nitrones, as well as stereoelectronic tunability of the nitrone moiety to optimize reactivity towards different alkyne reaction partners. Herein we discuss recent advances in the development of SPANC reactions and their applications in bioorthogonal labeling. Crown
Copyright © 2014. Published by Elsevier Ltd. All rights reserved.

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Year:  2014        PMID: 25022431     DOI: 10.1016/j.cbpa.2014.05.023

Source DB:  PubMed          Journal:  Curr Opin Chem Biol        ISSN: 1367-5931            Impact factor:   8.822


  9 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.  Branched Polyhedral Oligomeric Silsesquioxane Nanoparticles Prepared via Strain-Promoted 1,3-Dipolar Cycloadditions.

Authors:  Petr A Ledin; Weinan Xu; Frédéric Friscourt; Geert-Jan Boons; Vladimir V Tsukruk
Journal:  Langmuir       Date:  2015-07-14       Impact factor: 3.882

3.  Sterically Shielded, Stabilized Nitrile Imine for Rapid Bioorthogonal Protein Labeling in Live Cells.

Authors:  Peng An; Tracey M Lewandowski; Tuğçe G Erbay; Peng Liu; Qing Lin
Journal:  J Am Chem Soc       Date:  2018-04-02       Impact factor: 15.419

4.  Large-Scale Flow Photochemical Synthesis of Functionalized trans-Cyclooctenes Using Sulfonated Silica Gel.

Authors:  Ampofo Darko; Samantha J Boyd; Joseph M Fox
Journal:  Synthesis (Stuttg)       Date:  2018-12       Impact factor: 3.157

5.  Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.

Authors:  Yun Hu; Jessica M Roberts; Henry R Kilgore; Amirah S Mat Lani; Ronald T Raines; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2020-10-21       Impact factor: 15.419

6.  Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation.

Authors:  Han Zhang; William S Trout; Shuang Liu; Gabriel A Andrade; Devin A Hudson; Samuel L Scinto; Kevin T Dicker; Yi Li; Nikifar Lazouski; Joel Rosenthal; Colin Thorpe; Xinqiao Jia; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2016-04-27       Impact factor: 15.419

7.  Systematic Evaluation of Bioorthogonal Reactions in Live Cells with Clickable HaloTag Ligands: Implications for Intracellular Imaging.

Authors:  Heather E Murrey; Joshua C Judkins; Christopher W Am Ende; T Eric Ballard; Yinzhi Fang; Keith Riccardi; Li Di; Edward R Guilmette; Joel W Schwartz; Joseph M Fox; Douglas S Johnson
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

8.  Predicting reactivity for bioorthogonal cycloadditions involving nitrones.

Authors:  Masaya Nakajima; Didier A Bilodeau; John Paul Pezacki
Journal:  RSC Adv       Date:  2020-08-13       Impact factor: 4.036

9.  Cycloaddition of Strained Cyclic Alkenes and Ortho-Quinones: A Distortion/Interaction Analysis.

Authors:  Jorge Escorihuela; Wilhelmus J E Looijen; Xiao Wang; Adelia J A Aquino; Hans Lischka; Han Zuilhof
Journal:  J Org Chem       Date:  2020-10-26       Impact factor: 4.354

  9 in total

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