Direct formation and site-selective elaboration of methionine sulfoximine in polypeptides

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dc.citation.firstpage14101en_US
dc.citation.journalTitleChemical Scienceen_US
dc.citation.lastpage14105en_US
dc.citation.volumeNumber13en_US
dc.contributor.authorDing, Yuxuanen_US
dc.contributor.authorPedersen, Simon S.en_US
dc.contributor.authorLin, Alexen_US
dc.contributor.authorQian, Ruoyuen_US
dc.contributor.authorBall, Zachary T.en_US
dc.date.accessioned2022-12-13T19:11:17Zen_US
dc.date.available2022-12-13T19:11:17Zen_US
dc.date.issued2022en_US
dc.description.abstractSulfoximines are emerging moieties for medicinal and biological chemistry, due in part to their efficacy in selective inhibition of amide-forming enzymes such as γ-glutamylcysteine synthetase. While small-molecule sulfoximines such as methionine sulfoximine (MSO) and its derivatives are well studied, structures with methionine sulfoximine residues within complex polypeptides have been generally inaccessible. This paper describes a straightforward means of late-stage one-step oxidation of methionine residues within polypeptides to afford NH-sulfoximines. We also present chemoselective subsequent elaboration, most notably by copper(II)-mediated N–H cross-coupling at methionine sulfoximine residues with arylboronic acid reagents. This development serves as a strategy to incorporate diverse sulfoximine structures within natural polypeptides, and also identifies the methionine sulfoximine residue as a new site for bioorthogonal, chemoselective bioconjugation.en_US
dc.identifier.citationDing, Yuxuan, Pedersen, Simon S., Lin, Alex, et al.. "Direct formation and site-selective elaboration of methionine sulfoximine in polypeptides." <i>Chemical Science,</i> 13, (2022) Royal Society of Chemistry: 14101-14105. https://doi.org/10.1039/D2SC04220G.en_US
dc.identifier.digitald2sc04220gen_US
dc.identifier.doihttps://doi.org/10.1039/D2SC04220Gen_US
dc.identifier.urihttps://hdl.handle.net/1911/114094en_US
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.rightsThis Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licenceen_US
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/en_US
dc.titleDirect formation and site-selective elaboration of methionine sulfoximine in polypeptidesen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpublisher versionen_US
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