Literature DB >> 24796604

Acylazetine as a dienophile in bioorthogonal inverse electron-demand Diels-Alder ligation.

Sander B Engelsma1, Lianne I Willems, Claudia E van Paaschen, Sander I van Kasteren, Gijsbert A van der Marel, Herman S Overkleeft, Dmitri V Filippov.   

Abstract

A new bioorthogonal N-acylazetine tag, suitable for tetrazine mediated inverse electron-demand Diels-Alder conjugation, is developed. The tag is small and achiral. We demonstrate the usefulness of N-acylazetine-tetrazine based bioorthogonal chemistry in two-step activity-based protein profiling. The performance of the new tetrazinophile in the labeling of catalytically active proteasome subunits was comparable to that of the more sterically demanding norbornene tag.

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Year:  2014        PMID: 24796604     DOI: 10.1021/ol501049c

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  11 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.  Developing bioorthogonal probes to span a spectrum of reactivities.

Authors:  Sean S Nguyen; Jennifer A Prescher
Journal:  Nat Rev Chem       Date:  2020-07-21       Impact factor: 34.035

3.  Bioorthogonal chemistry.

Authors:  Samuel L Scinto; Didier A Bilodeau; Robert Hincapie; Wankyu Lee; Sean S Nguyen; Minghao Xu; Christopher W Am Ende; M G Finn; Kathrin Lang; Qing Lin; John Paul Pezacki; Jennifer A Prescher; Marc S Robillard; Joseph M Fox
Journal:  Nat Rev Methods Primers       Date:  2021-04-15

Review 4.  A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.

Authors:  Kiall F Suazo; Keun-Young Park; Mark D Distefano
Journal:  Chem Rev       Date:  2021-04-06       Impact factor: 72.087

5.  Discovery of new mutually orthogonal bioorthogonal cycloaddition pairs through computational screening.

Authors:  Maruthi Kumar Narayanam; Yong Liang; K N Houk; Jennifer M Murphy
Journal:  Chem Sci       Date:  2015-11-11       Impact factor: 9.825

6.  Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni-Lindsey Reaction.

Authors:  Selma Eising; Francis Lelivelt; Kimberly M Bonger
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-08       Impact factor: 15.336

Review 7.  Bio-orthogonal Fluorescent Labelling of Biopolymers through Inverse-Electron-Demand Diels-Alder Reactions.

Authors:  Eszter Kozma; Orsolya Demeter; Péter Kele
Journal:  Chembiochem       Date:  2017-02-01       Impact factor: 3.164

8.  Enzymatic modification of 5'-capped RNA with a 4-vinylbenzyl group provides a platform for photoclick and inverse electron-demand Diels-Alder reaction.

Authors:  Josephin Marie Holstein; Daniela Stummer; Andrea Rentmeister
Journal:  Chem Sci       Date:  2014-11-26       Impact factor: 9.825

9.  Isomeric triazines exhibit unique profiles of bioorthogonal reactivity.

Authors:  David N Kamber; Sean S Nguyen; Fang Liu; Jeffrey S Briggs; Hui-Wen Shih; R David Row; Zane G Long; K N Houk; Yong Liang; Jennifer A Prescher
Journal:  Chem Sci       Date:  2019-08-21       Impact factor: 9.825

Review 10.  Bioorthogonal Ligations and Cleavages in Chemical Biology.

Authors:  Youshan Li; Hua Fu
Journal:  ChemistryOpen       Date:  2020-08-14       Impact factor: 2.911

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