Literature DB >> 24027163

Norbornenes in inverse electron-demand Diels-Alder reactions.

Milan Vrabel1, Patrick Kölle, Korbinian M Brunner, Michael J Gattner, Verónica López-Carrillo, Regina de Vivie-Riedle, Thomas Carell.   

Abstract

Significant differences in the reactivity of norbornene derivatives in the inverse electron-demand Diels-Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed. Quantum-chemical calculations were used to rationalize and support the observed experimental data.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  inverse electron-demand Diels-Alder reactions; kinetics; norbornene; quantum-chemical calculations

Mesh：

Substances：

Year:  2013        PMID： 24027163     DOI： 10.1002/chem.201301838

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  12 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.  3,6-Substituted-1,2,4,5-tetrazines: tuning reaction rates for staged labeling applications.

Authors:  Danzhu Wang; Weixuan Chen; Yueqin Zheng; Chaofeng Dai; Ke Wang; Bowen Ke; Binghe Wang
Journal:  Org Biomol Chem       Date:  2014-06-21       Impact factor: 3.876

3.  Stable, Reactive, and Orthogonal Tetrazines: Dispersion Forces Promote the Cycloaddition with Isonitriles.

Authors:  Julian Tu; Dennis Svatunek; Saba Parvez; Albert C Liu; Brian J Levandowski; Hannah J Eckvahl; Randall T Peterson; Kendall N Houk; Raphael M Franzini
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-06       Impact factor: 16.823

4.  Kinetic studies of inverse electron demand Diels-Alder reactions (iEDDA) of norbornenes and 3,6-dipyridin-2-yl-1,2,4,5-tetrazine.

Authors:  Astrid-Caroline Knall; Manuel Hollauf; Christian Slugovc
Journal:  Tetrahedron Lett       Date:  2014-08-20       Impact factor: 2.415

5.  A Minimal, Unstrained S-Allyl Handle for Pre-Targeting Diels-Alder Bioorthogonal Labeling in Live Cells.

Authors:  Bruno L Oliveira; Zijian Guo; Omar Boutureira; Ana Guerreiro; Gonzalo Jiménez-Osés; Gonçalo J L Bernardes
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-20       Impact factor: 15.336

6.  Approach Matters: The Kinetics of Interfacial Inverse-Electron Demand Diels-Alder Reactions.

Authors:  Rickdeb Sen; Digvijay Gahtory; Jorge Escorihuela; Judith Firet; Sidharam P Pujari; Han Zuilhof
Journal:  Chemistry       Date:  2017-08-23       Impact factor: 5.236

7.  PEGylation and Dimerization of Expressed Proteins under Near Equimolar Conditions with Potassium 2-Pyridyl Acyltrifluoroborates.

Authors:  Christopher J White; Jeffrey W Bode
Journal:  ACS Cent Sci       Date:  2018-01-05       Impact factor: 14.553

8.  The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions.

Authors:  Sebastian J Siegl; Rastislav Dzijak; Arcadio Vázquez; Radek Pohl; Milan Vrabel
Journal:  Chem Sci       Date:  2017-03-01       Impact factor: 9.825

9.  Tetrazine-Containing Amino Acid for Peptide Modification and Live Cell Labeling.

Authors:  Zhongqiu Ni; Lanxia Zhou; Xu Li; Jing Zhang; Shouliang Dong
Journal:  PLoS One       Date:  2015-11-04       Impact factor: 3.240

10.  A benzylic linker promotes methyltransferase catalyzed norbornene transfer for rapid bioorthogonal tetrazine ligation.

Authors:  F Muttach; N Muthmann; D Reichert; L Anhäuser; A Rentmeister
Journal:  Chem Sci       Date:  2017-10-10       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.