{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T11:42:24Z","timestamp":1790336544623,"version":"4.1.0"},"reference-count":13,"publisher":"Royal Society of Chemistry (RSC)","issue":"15","license":[{"start":{"date-parts":[[2022,3,24]],"date-time":"2022-03-24T00:00:00Z","timestamp":1648080000000},"content-version":"vor","delay-in-days":82,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/3.0\/"}],"content-domain":{"domain":["rsc.org"],"crossmark-restriction":true},"short-container-title":["Org. Biomol. Chem."],"abstract":"<jats:p>Thiols are commonly exploited as nucleophiles in biomolecules, but phosphines less so. In this work we show that conjugate addition of phosphines into dehydroalanine is a practical approach to peptide modification to form a phosphonium ion product.<\/jats:p>","DOI":"10.1039\/d2ob00410k","type":"journal-article","created":{"date-parts":[[2022,3,24]],"date-time":"2022-03-24T20:05:00Z","timestamp":1648152300000},"page":"3081-3085","update-policy":"https:\/\/doi.org\/10.1039\/rsc_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Phosphine addition to dehydroalanine for peptide modification"],"prefix":"10.1039","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5057-4315","authenticated-orcid":false,"given":"Minglong","family":"Liu","sequence":"first","affiliation":[{"name":"Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute of Molecular and Life Sciences, VU Amsterdam, De Boelelaan 1108, 1081HZ Amsterdam, The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miha","family":"Sovrovic","sequence":"additional","affiliation":[{"name":"Department of Chemical Biology & Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5298-9186","authenticated-orcid":false,"given":"Hiroaki","family":"Suga","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-0033 Tokyo, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4796-0557","authenticated-orcid":false,"given":"Seino A. K.","family":"Jongkees","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute of Molecular and Life Sciences, VU Amsterdam, De Boelelaan 1108, 1081HZ Amsterdam, The Netherlands"},{"name":"Department of Chemical Biology & Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands"},{"name":"Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-0033 Tokyo, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"292","published-online":{"date-parts":[[2022]]},"reference":[{"key":"D2OB00410K\/cit1a\/1","doi-asserted-by":"crossref","first-page":"2174","DOI":"10.1021\/cr500399p","volume":"115","author":"Boutureira","year":"2015","journal-title":"Chem. Rev."},{"key":"D2OB00410K\/cit1b\/1","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1002\/cbic.201500667","volume":"17","author":"Gunnoo","year":"2016","journal-title":"ChemBioChem"},{"key":"D2OB00410K\/cit2a\/1","doi-asserted-by":"crossref","first-page":"1617","DOI":"10.1039\/c1sc00185j","volume":"2","author":"Chalker","year":"2011","journal-title":"Chem. Sci."},{"key":"D2OB00410K\/cit2b\/1","doi-asserted-by":"crossref","first-page":"13470","DOI":"10.1039\/C5CC05469A","volume":"51","author":"Morrison","year":"2015","journal-title":"Chem. Commun."},{"key":"D2OB00410K\/cit3\/1","doi-asserted-by":"crossref","first-page":"1474","DOI":"10.1039\/C6SC04381J","volume":"8","author":"Jongkees","year":"2017","journal-title":"Chem. Sci."},{"key":"D2OB00410K\/cit4\/1","doi-asserted-by":"crossref","first-page":"456","DOI":"10.1002\/cbic.201500697","volume":"17","author":"Lee","year":"2016","journal-title":"ChemBioChem"},{"key":"D2OB00410K\/cit5\/1","doi-asserted-by":"crossref","first-page":"4720","DOI":"10.1021\/acs.biochem.6b00622","volume":"55","author":"Scian","year":"2016","journal-title":"Biochemistry"},{"key":"D2OB00410K\/cit6\/1","doi-asserted-by":"crossref","first-page":"6722","DOI":"10.1021\/ja071990s","volume":"129","author":"Zhu","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"D2OB00410K\/cit7\/1","doi-asserted-by":"crossref","first-page":"2102","DOI":"10.1002\/anie.200704390","volume":"47","author":"Hanes","year":"2008","journal-title":"Angew. Chem., Int. Ed."},{"key":"D2OB00410K\/cit8\/1","doi-asserted-by":"crossref","first-page":"5634","DOI":"10.1021\/ja00040a024","volume":"114","author":"Palmer","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"D2OB00410K\/cit9\/1","doi-asserted-by":"crossref","first-page":"9382","DOI":"10.1021\/jacs.5b04501","volume":"137","author":"Koopmans","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"D2OB00410K\/cit10\/1","doi-asserted-by":"crossref","first-page":"12698","DOI":"10.1002\/chem.201902907","volume":"25","author":"Vries","year":"2019","journal-title":"Chem. \u2013 Eur. J."},{"key":"D2OB00410K\/cit11\/1","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1002\/em.20554","volume":"51","author":"Frantz","year":"2010","journal-title":"Environ. Mol. Mutagen."}],"container-title":["Organic &amp; Biomolecular Chemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/pubs.rsc.org\/en\/content\/articlepdf\/2022\/OB\/D2OB00410K","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T04:21:23Z","timestamp":1782966083000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.rsc.org\/ob\/article\/20\/15\/3081-3085\/778379"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022]]},"references-count":13,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2022,4,13]]}},"URL":"https:\/\/doi.org\/10.1039\/d2ob00410k","relation":{},"ISSN":["1477-0520","1477-0539"],"issn-type":[{"value":"1477-0520","type":"print"},{"value":"1477-0539","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022]]}}}