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Chemically triggered crosslinking with bioorthogonal cyclopropenones
We report a proximity-driven crosslinking strategy featuring bioorthogonal cyclopropenones. These motifs react with phosphines to form electrophilic ketene-ylides. Such intermediates can be trapped by neighboring proteins to form covalent adducts. Successful crosslinking was achieved using a model s...
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| Published in: | Chemical communications (Cambridge, England) England), 2020-09, Vol.56 (74), p.1883-1886 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c454t-5184bd5d6d754bd31f5a156c5bbed6072460b35df663eebd1e6dc418513257d53 |
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| cites | cdi_FETCH-LOGICAL-c454t-5184bd5d6d754bd31f5a156c5bbed6072460b35df663eebd1e6dc418513257d53 |
| container_end_page | 1886 |
| container_issue | 74 |
| container_start_page | 1883 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 56 |
| creator | Row, R. David Nguyen, Sean S Ferreira, Andrew J Prescher, Jennifer A |
| description | We report a proximity-driven crosslinking strategy featuring bioorthogonal cyclopropenones. These motifs react with phosphines to form electrophilic ketene-ylides. Such intermediates can be trapped by neighboring proteins to form covalent adducts. Successful crosslinking was achieved using a model split reporter, and the rate of crosslinking could be tuned using different phosphine triggers. We further demonstrated that the reaction can be performed in cell lysate. Based on these features, we anticipate that cyclopropenones will enable unique studies of protein-protein and other biomolecule interactions.
Bioorthogonal cyclopropenones can be chemically triggered to crosslink interacting biomolecules. |
| doi_str_mv | 10.1039/d0cc04600k |
| format | article |
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Bioorthogonal cyclopropenones can be chemically triggered to crosslink interacting biomolecules.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d0cc04600k</identifier><identifier>PMID: 32808608</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Adducts ; Bacteria - chemistry ; Bacteria - cytology ; Biocompatible Materials - chemical synthesis ; Biocompatible Materials - chemistry ; Biomolecules ; Cross-Linking Reagents - chemical synthesis ; Cross-Linking Reagents - chemistry ; Crosslinking ; Cyclopropanes - chemistry ; Models, Molecular ; Molecular Structure ; Phosphines ; Phosphines - chemistry ; Proteins</subject><ispartof>Chemical communications (Cambridge, England), 2020-09, Vol.56 (74), p.1883-1886</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c454t-5184bd5d6d754bd31f5a156c5bbed6072460b35df663eebd1e6dc418513257d53</citedby><cites>FETCH-LOGICAL-c454t-5184bd5d6d754bd31f5a156c5bbed6072460b35df663eebd1e6dc418513257d53</cites><orcidid>0000-0002-9250-4702 ; 0000-0002-1801-5521</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32808608$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Row, R. David</creatorcontrib><creatorcontrib>Nguyen, Sean S</creatorcontrib><creatorcontrib>Ferreira, Andrew J</creatorcontrib><creatorcontrib>Prescher, Jennifer A</creatorcontrib><title>Chemically triggered crosslinking with bioorthogonal cyclopropenones</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>We report a proximity-driven crosslinking strategy featuring bioorthogonal cyclopropenones. These motifs react with phosphines to form electrophilic ketene-ylides. Such intermediates can be trapped by neighboring proteins to form covalent adducts. Successful crosslinking was achieved using a model split reporter, and the rate of crosslinking could be tuned using different phosphine triggers. We further demonstrated that the reaction can be performed in cell lysate. Based on these features, we anticipate that cyclopropenones will enable unique studies of protein-protein and other biomolecule interactions.
Bioorthogonal cyclopropenones can be chemically triggered to crosslink interacting biomolecules.</description><subject>Adducts</subject><subject>Bacteria - chemistry</subject><subject>Bacteria - cytology</subject><subject>Biocompatible Materials - chemical synthesis</subject><subject>Biocompatible Materials - chemistry</subject><subject>Biomolecules</subject><subject>Cross-Linking Reagents - chemical synthesis</subject><subject>Cross-Linking Reagents - chemistry</subject><subject>Crosslinking</subject><subject>Cyclopropanes - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Phosphines</subject><subject>Phosphines - chemistry</subject><subject>Proteins</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kUtLxDAUhYMojo5u3CsVNyJUk-bRuhGkPnHAjYK70CZpJ2OmqUlHmX9v5uH4WJjNvXA_Ts69B4A9BE8RxOdnEgoBCYPwdQ1sIcxITEn2sj7r6XmcYkJ7YNv7EQwP0WwT9HCSwYzBbAtc5UM11qIwZhp1Tte1ckpGwlnvjW5edVNHH7obRqW21nVDW9umMJGYCmNbZ1vV2Eb5HbBRFcar3WXtg-eb66f8Lh483t7nl4NYEEq6mKKMlJJKJlMaGowqWiDKBC1LJRlMk7BDiamsGMNKlRIpJgVBGUU4oamkuA8uFrrtpBwrKVTTucLw1ulx4abcFpr_njR6yGv7zlMKEUpJEDheCjj7NlG-42PthTKmaJSdeJ4QHEyGD9OAHv1BR3biwvIziuBw5SRFgTpZUPOLOVWtzCDIZ-HwK5jn83AeAnzw0_4K_UojAIcLwHmxmn6ny1tZBWb_PwZ_AsOUoJY</recordid><startdate>20200917</startdate><enddate>20200917</enddate><creator>Row, R. 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We further demonstrated that the reaction can be performed in cell lysate. Based on these features, we anticipate that cyclopropenones will enable unique studies of protein-protein and other biomolecule interactions.
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| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-09, Vol.56 (74), p.1883-1886 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Adducts Bacteria - chemistry Bacteria - cytology Biocompatible Materials - chemical synthesis Biocompatible Materials - chemistry Biomolecules Cross-Linking Reagents - chemical synthesis Cross-Linking Reagents - chemistry Crosslinking Cyclopropanes - chemistry Models, Molecular Molecular Structure Phosphines Phosphines - chemistry Proteins |
| title | Chemically triggered crosslinking with bioorthogonal cyclopropenones |
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