Photo-accelerated "click" reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation
We constructed a library of diarylsydnone (DASyd) candidates in search of a photoclickable reaction toward alkynes, enabling an ultra-accelerated reactivity, while suppressing the background cycloaddition in the dark. The in vitro and in vivo protein labelling experiments revealed that the photo-acc...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2019, Vol.55 (5), p.7187-719 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Zhang, Xiaocui Wu, Xueting Jiang, Shichao Gao, Jingshuo Yao, Zhuojun Deng, Jiajie Zhang, Linmeng Yu, Zhipeng |
| description | We constructed a library of diarylsydnone (DASyd) candidates in search of a photoclickable reaction toward alkynes, enabling an ultra-accelerated reactivity, while suppressing the background cycloaddition in the dark. The
in vitro
and
in vivo
protein labelling experiments revealed that the photo-accelerated DASyd-alkyne cycloaddition exhibits robust selectivity.
A novel photo-click ligation reaction between diarylsydnones and ring-strained alkynes, exhibiting decent bioorthogonality, was established under 405 nm light irradiation. |
| doi_str_mv | 10.1039/c9cc02882j |
| format | Article |
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in vitro
and
in vivo
protein labelling experiments revealed that the photo-accelerated DASyd-alkyne cycloaddition exhibits robust selectivity.
A novel photo-click ligation reaction between diarylsydnones and ring-strained alkynes, exhibiting decent bioorthogonality, was established under 405 nm light irradiation.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc02882j</identifier><identifier>PMID: 31165109</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkynes ; Crystallography ; Cycloaddition ; Selectivity</subject><ispartof>Chemical communications (Cambridge, England), 2019, Vol.55 (5), p.7187-719</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-b0141df16727b6de6eff06f76fafd6d6eb05ca7e7b35a5cd25ca84cb693828da3</citedby><cites>FETCH-LOGICAL-c429t-b0141df16727b6de6eff06f76fafd6d6eb05ca7e7b35a5cd25ca84cb693828da3</cites><orcidid>0000-0001-6411-6078</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31165109$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Xiaocui</creatorcontrib><creatorcontrib>Wu, Xueting</creatorcontrib><creatorcontrib>Jiang, Shichao</creatorcontrib><creatorcontrib>Gao, Jingshuo</creatorcontrib><creatorcontrib>Yao, Zhuojun</creatorcontrib><creatorcontrib>Deng, Jiajie</creatorcontrib><creatorcontrib>Zhang, Linmeng</creatorcontrib><creatorcontrib>Yu, Zhipeng</creatorcontrib><title>Photo-accelerated "click" reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>We constructed a library of diarylsydnone (DASyd) candidates in search of a photoclickable reaction toward alkynes, enabling an ultra-accelerated reactivity, while suppressing the background cycloaddition in the dark. The
in vitro
and
in vivo
protein labelling experiments revealed that the photo-accelerated DASyd-alkyne cycloaddition exhibits robust selectivity.
A novel photo-click ligation reaction between diarylsydnones and ring-strained alkynes, exhibiting decent bioorthogonality, was established under 405 nm light irradiation.</description><subject>Alkynes</subject><subject>Crystallography</subject><subject>Cycloaddition</subject><subject>Selectivity</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp90c1v2yAUAHA0dVradJfdW7npZarkDbCN4VhZ7T4UqT100m4WhkdC6kAKjqr89yNNlko9lAug9-Pp8R5CXwj-RnAhviuhFKac08UHdEwKVuZVyf8ebc-VyOuirEboJMYFTotU_BMaFYSwimBxjNz93A8-l0pBD0EOoLOJ6q16nGQBpBqsd1kHwzOAy7SVYdPHjXbeQcyk01mwbpbHIUjr0kvZP262EeND1lnvwzD3M-9kn_V2Jre5TtFHI_sIn_f7GP25vXlofubTux-_mutprkoqhrzDpCTaEFbTumMaGBiDmamZkUYzzaDDlZI11F1RyUppmm68VB0TBadcy2KMvu7yroJ_WkMc2qWN6Yu9dODXsaW0pJwwUeNEL9_QhV-HVPROYUIEp0ld7ZQKPsYApl0Fu0z9aAlut1NoG9E0L1P4nfD5PuW6W4I-0P9tT-BiB0JUh-jrGNuVNsmcvWeKfyWvmaU</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Zhang, Xiaocui</creator><creator>Wu, Xueting</creator><creator>Jiang, Shichao</creator><creator>Gao, Jingshuo</creator><creator>Yao, Zhuojun</creator><creator>Deng, Jiajie</creator><creator>Zhang, Linmeng</creator><creator>Yu, Zhipeng</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6411-6078</orcidid></search><sort><creationdate>2019</creationdate><title>Photo-accelerated "click" reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation</title><author>Zhang, Xiaocui ; Wu, Xueting ; Jiang, Shichao ; Gao, Jingshuo ; Yao, Zhuojun ; Deng, Jiajie ; Zhang, Linmeng ; Yu, Zhipeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-b0141df16727b6de6eff06f76fafd6d6eb05ca7e7b35a5cd25ca84cb693828da3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkynes</topic><topic>Crystallography</topic><topic>Cycloaddition</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xiaocui</creatorcontrib><creatorcontrib>Wu, Xueting</creatorcontrib><creatorcontrib>Jiang, Shichao</creatorcontrib><creatorcontrib>Gao, Jingshuo</creatorcontrib><creatorcontrib>Yao, Zhuojun</creatorcontrib><creatorcontrib>Deng, Jiajie</creatorcontrib><creatorcontrib>Zhang, Linmeng</creatorcontrib><creatorcontrib>Yu, Zhipeng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Xiaocui</au><au>Wu, Xueting</au><au>Jiang, Shichao</au><au>Gao, Jingshuo</au><au>Yao, Zhuojun</au><au>Deng, Jiajie</au><au>Zhang, Linmeng</au><au>Yu, Zhipeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photo-accelerated "click" reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2019</date><risdate>2019</risdate><volume>55</volume><issue>5</issue><spage>7187</spage><epage>719</epage><pages>7187-719</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>We constructed a library of diarylsydnone (DASyd) candidates in search of a photoclickable reaction toward alkynes, enabling an ultra-accelerated reactivity, while suppressing the background cycloaddition in the dark. The
in vitro
and
in vivo
protein labelling experiments revealed that the photo-accelerated DASyd-alkyne cycloaddition exhibits robust selectivity.
A novel photo-click ligation reaction between diarylsydnones and ring-strained alkynes, exhibiting decent bioorthogonality, was established under 405 nm light irradiation.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31165109</pmid><doi>10.1039/c9cc02882j</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-6411-6078</orcidid></addata></record> |
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| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2019, Vol.55 (5), p.7187-719 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2242816970 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkynes Crystallography Cycloaddition Selectivity |
| title | Photo-accelerated "click" reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation |
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