{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,5]],"date-time":"2026-09-05T14:34:58Z","timestamp":1788618898284,"version":"build-2803163510"},"reference-count":38,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2018,6,28]],"date-time":"2018-06-28T00:00:00Z","timestamp":1530144000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2018,8,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Bioorthogonal chemistry can be used for the selective modification of biomolecules without interfering with any other functionality that might be present. Recent developments in the field include orthogonal bioorthogonal reactions to modify multiple biomolecules simultaneously. During our research, we observed that the reaction rates for the bioorthogonal inverse\u2010electron\u2010demand Diels\u2013Alder (iEDDA) reactions between nonstrained vinylboronic acids (VBAs) and dipyridyl\u2010\n                    <jats:italic>s<\/jats:italic>\n                    \u2010tetrazines were exceptionally higher than those between VBAs and tetrazines bearing a methyl or phenyl substituent. As VBAs are mild Lewis acids, we hypothesised that coordination of the pyridyl nitrogen atom to the boronic acid promoted tetrazine ligation. Herein, we explore the molecular basis and scope of VBA\u2013tetrazine ligation in more detail and benefit from its unique reactivity in the simultaneous orthogonal tetrazine labelling of two proteins modified with VBA and norbornene, a widely used strained alkene. We further show that the two orthogonal iEDDA reactions can be performed in living cells by labelling the proteasome by using a nonselective probe equipped with a VBA and a subunit\u2010selective VBA bearing a norbornene moiety.\n                  <\/jats:p>","DOI":"10.1002\/cbic.201800275","type":"journal-article","created":{"date-parts":[[2018,5,28]],"date-time":"2018-05-28T09:14:35Z","timestamp":1527498875000},"page":"1648-1652","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Coordination\u2010Assisted Bioorthogonal Chemistry: Orthogonal Tetrazine Ligation with Vinylboronic Acid and a Strained Alkene"],"prefix":"10.1002","volume":"19","author":[{"given":"Selma","family":"Eising","sequence":"first","affiliation":[{"name":"Department of Biomolecular Chemistry Institute for Molecules and Materials Radboud University  Heyendaalseweg 135 6525\u2005AJ Nijmegen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo\u2010Tao","family":"Xin","sequence":"additional","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333\u2005CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fleur","family":"Kleinpenning","sequence":"additional","affiliation":[{"name":"Department of Biomolecular Chemistry Institute for Molecules and Materials Radboud University  Heyendaalseweg 135 6525\u2005AJ Nijmegen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jurriaan J. A.","family":"Heming","sequence":"additional","affiliation":[{"name":"Department of Biomolecular Chemistry Institute for Molecules and Materials Radboud University  Heyendaalseweg 135 6525\u2005AJ Nijmegen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bogdan I.","family":"Florea","sequence":"additional","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333\u2005CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Herman S.","family":"Overkleeft","sequence":"additional","affiliation":[{"name":"Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333\u2005CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9498-2620","authenticated-orcid":false,"given":"Kimberly M.","family":"Bonger","sequence":"additional","affiliation":[{"name":"Department of Biomolecular Chemistry Institute for Molecules and Materials Radboud University  Heyendaalseweg 135 6525\u2005AJ Nijmegen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,6,28]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2014.07.002"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB01632G"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc500028d"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB00126B"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2013.08.004"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60049a"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201600607"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00184C"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja8053805"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2013.07.031"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc8004446"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja3060436"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202122"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201202122"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201208991"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201208991"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC06435F"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)97188-0"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(199812)1998:12<2885::AID-EJOC2885>3.0.CO;2-L"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201605271"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201605271"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.7b00796"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2015.07.006"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2015.07.021"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201104389"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201104389"},{"key":"e_1_2_2_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200923"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201200923"},{"key":"e_1_2_2_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc300181n"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309847"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309847"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201501727"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527639328"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol902573x"},{"key":"e_1_2_2_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1250"},{"key":"e_1_2_2_30_1","volume-title":"Heterocyclic Chemistry at a Glance","author":"Joule J. 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