Photo-click chemistry strategies for spatiotemporal control of metal-free ligation, labeling, and surface derivatization
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- Selvanathan Arumugam
- Department of Chemistry, University of Georgia, Athens, GA 30602, USA
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- Sara V. Orski
- Department of Chemistry, University of Georgia, Athens, GA 30602, USA
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- Ngalle Eric Mbua
- Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA
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- Christopher McNitt
- Department of Chemistry, University of Georgia, Athens, GA 30602, USA
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- Geert-Jan Boons
- Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA
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- Jason Locklin
- Department of Chemistry, University of Georgia, Athens, GA 30602, USA
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- Vladimir V. Popik
- Department of Chemistry, University of Georgia, Athens, GA 30602, USA
書誌事項
- 公開日
- 2013-05-23
- DOI
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- 10.1351/pac-con-13-01-08
- 公開者
- Walter de Gruyter GmbH
この論文をさがす
説明
<jats:p>Three photo-click ligation strategies described in this account provide scientists with efficient and selective tools for derivatization of various molecules, polymers, and surfaces. Fast photochemical reactions that are utilized in these techniques permit spatiotemporal control of the process. The absence of activating reagents and catalysts, as well as compatibility with aqueous media, makes photo-click ligations suitable for biomedical applications. The first of these approaches relies on the photochemical decarbonylation of cyclopropenones to produce cyclooctynes. The latter undergo rapid catalyst-free strain-promoted azide–alkyne cycloaddition (SPAAC) to azide-tagged substrates. The second method is based on a very fast (>10<jats:sup>4</jats:sup>M<jats:sup>–1</jats:sup>s<jats:sup>–1</jats:sup>) light-triggered hetero-Diels–Alder reaction and permits efficient derivatization of substrates bearing vinyl ether moiety. An even faster reaction between photochemically generated naphthoquinone methides (<jats:italic>o</jats:italic>NQMs) and thiols (~2 × 10<jats:sup>5</jats:sup>M<jats:sup>–1</jats:sup>s<jats:sup>–1</jats:sup>) serves as a basis for a third method. This thiol photo-click chemistry allows for the selective derivatization of thiol-functionalized substrates or labeling of free cysteine residues in proteins. The thioether linkage produced by the reaction of<jats:italic>o</jats:italic>NQMs and a thiol is stable under ambient conditions, but can be cleaved by UV irradiation, regenerating free thiol. This feature permits the removal or replacement of immobilized compounds, as well as traceless substrate release.</jats:p>
収録刊行物
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- Pure and Applied Chemistry
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Pure and Applied Chemistry 85 (7), 1499-1513, 2013-05-23
Walter de Gruyter GmbH