{"id":"https://openalex.org/W3001757596","doi":"https://doi.org/10.1002/ange.201800860","title":"Site\u2010Selective Cysteine\u2013Cyclooctyne Conjugation","display_name":"Site\u2010Selective Cysteine\u2013Cyclooctyne Conjugation","publication_year":2018,"publication_date":"2018-03-25","ids":{"openalex":"https://openalex.org/W3001757596","doi":"https://doi.org/10.1002/ange.201800860","mag":"3001757596"},"language":"en","primary_location":{"id":"doi:10.1002/ange.201800860","doi":"https://doi.org/10.1002/ange.201800860","is_oa":false,"landing_page_url":"https://doi.org/10.1002/ange.201800860","pdf_url":null,"source":{"id":"https://openalex.org/S4210200754","display_name":"Angewandte Chemie","issn_l":"0044-8249","issn":["0044-8249","0932-2140","1521-3757"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angewandte Chemie","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5100458146","display_name":"Chi Zhang","orcid":"https://orcid.org/0000-0001-9519-7456","observed_orcids":["https://orcid.org/0000-0001-9519-7456"]},"institutions":[{"id":"https://openalex.org/I63966007","display_name":"Massachusetts Institute of Technology","ror":"https://ror.org/042nb2s44","country_code":"US","type":"education","lineage":["https://openalex.org/I63966007"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Chi Zhang","raw_affiliation_strings":["Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA"],"raw_orcid":"https://orcid.org/0000-0001-9519-7456","affiliations":[{"raw_affiliation_string":"Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA","institution_ids":["https://openalex.org/I63966007"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5027224776","display_name":"Peng Dai","orcid":"https://orcid.org/0000-0002-4581-3473","observed_orcids":["https://orcid.org/0000-0002-4581-3473"]},"institutions":[{"id":"https://openalex.org/I63966007","display_name":"Massachusetts Institute of Technology","ror":"https://ror.org/042nb2s44","country_code":"US","type":"education","lineage":["https://openalex.org/I63966007"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Peng Dai","raw_affiliation_strings":["Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA"],"raw_orcid":"https://orcid.org/0000-0002-4581-3473","affiliations":[{"raw_affiliation_string":"Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA","institution_ids":["https://openalex.org/I63966007"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5042059275","display_name":"Alexander A. Vinogradov","orcid":"https://orcid.org/0000-0002-8899-0533","observed_orcids":["https://orcid.org/0000-0002-8899-0533"]},"institutions":[{"id":"https://openalex.org/I63966007","display_name":"Massachusetts Institute of Technology","ror":"https://ror.org/042nb2s44","country_code":"US","type":"education","lineage":["https://openalex.org/I63966007"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Alexander A. Vinogradov","raw_affiliation_strings":["Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA","institution_ids":["https://openalex.org/I63966007"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5081812580","display_name":"Zachary P. Gates","orcid":"https://orcid.org/0000-0003-0588-6157","observed_orcids":["https://orcid.org/0000-0003-0588-6157"]},"institutions":[{"id":"https://openalex.org/I63966007","display_name":"Massachusetts Institute of Technology","ror":"https://ror.org/042nb2s44","country_code":"US","type":"education","lineage":["https://openalex.org/I63966007"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Zachary P. Gates","raw_affiliation_strings":["Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA","institution_ids":["https://openalex.org/I63966007"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5021760386","display_name":"Bradley L. Pentelute","orcid":"https://orcid.org/0000-0002-7242-801X","observed_orcids":["https://orcid.org/0000-0002-7242-801X"]},"institutions":[{"id":"https://openalex.org/I63966007","display_name":"Massachusetts Institute of Technology","ror":"https://ror.org/042nb2s44","country_code":"US","type":"education","lineage":["https://openalex.org/I63966007"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Bradley L. Pentelute","raw_affiliation_strings":["Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA"],"raw_orcid":"https://orcid.org/0000-0002-7242-801X","affiliations":[{"raw_affiliation_string":"Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA","institution_ids":["https://openalex.org/I63966007"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5021760386"],"corresponding_institution_ids":["https://openalex.org/I63966007"],"apc_list":{"value":5790,"currency":"USD","value_usd":5790},"apc_paid":null,"fwci":1.1257,"has_fulltext":false,"cited_by_count":23,"citation_normalized_percentile":{"value":0.73584468,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"130","issue":"22","first_page":"6569","last_page":"6573"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11440","display_name":"Click Chemistry and Applications","score":0.9916999936103821,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T11440","display_name":"Click Chemistry and Applications","score":0.9916999936103821,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.0024999999441206455,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T13326","display_name":"Biochemical and Structural Characterization","score":0.0013000000035390258,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/thiol-yne-reaction","display_name":"thiol-yne reaction","score":0.8330000042915344},{"id":"https://openalex.org/keywords/peptide-tags","display_name":"peptide tags","score":0.5019999742507935},{"id":"https://openalex.org/keywords/fluorescent-probes","display_name":"fluorescent probes","score":0.6899999976158142},{"id":"https://openalex.org/keywords/affinity-tags","display_name":"affinity tags","score":0.9509999752044678},{"id":"https://openalex.org/keywords/trastuzumab","display_name":"trastuzumab","score":0.859000027179718},{"id":"https://openalex.org/keywords/green-fluorescent-protein","display_name":"green fluorescent protein","score":0.9869999885559082},{"id":"https://openalex.org/keywords/protein-modification","display_name":"protein modification","score":0.37400001287460327}],"concepts":[{"id":"https://openalex.org/C2779201268","wikidata":"https://www.wikidata.org/wiki/Q186474","display_name":"Cysteine","level":3,"score":0.732717752456665},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6837501525878906},{"id":"https://openalex.org/C2779281246","wikidata":"https://www.wikidata.org/wiki/Q172847","display_name":"Peptide","level":2,"score":0.6504858732223511},{"id":"https://openalex.org/C2781338088","wikidata":"https://www.wikidata.org/wiki/Q903495","display_name":"Residue (chemistry)","level":2,"score":0.5441222786903381},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.4962323307991028},{"id":"https://openalex.org/C91881484","wikidata":"https://www.wikidata.org/wiki/Q191807","display_name":"Fluorescence","level":2,"score":0.4533816874027252},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4271330237388611},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.2874905467033386},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.14656230807304382},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1002/ange.201800860","doi":"https://doi.org/10.1002/ange.201800860","is_oa":false,"landing_page_url":"https://doi.org/10.1002/ange.201800860","pdf_url":null,"source":{"id":"https://openalex.org/S4210200754","display_name":"Angewandte Chemie","issn_l":"0044-8249","issn":["0044-8249","0932-2140","1521-3757"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angewandte Chemie","raw_type":"journal-article"},{"id":"mag:3001757596","doi":null,"is_oa":false,"landing_page_url":"https://dspace.mit.edu/handle/1721.1/123516","pdf_url":null,"source":{"id":"https://openalex.org/S4306522653","display_name":"PMC","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"journal"},"license":null,"license_id":null,"version":null,"is_accepted":false,"is_published":false,"raw_source_name":"PMC","raw_type":null}],"best_oa_location":null,"sustainable_development_goals":[],"sustainable_development_goals_aurora":[{"display_name":"Clean water and sanitation","id":"https://metadata.un.org/sdg/6","score":0.8100000023841858}],"study_designs":[],"awards":[{"id":"https://openalex.org/G652502287","display_name":null,"funder_award_id":"GM110535","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G7988586476","display_name":null,"funder_award_id":"023504-001","funder_id":"https://openalex.org/F4320332180","funder_display_name":"Defense Advanced Research Projects Agency"}],"funders":[{"id":"https://openalex.org/F4320332180","display_name":"Defense Advanced Research Projects Agency","ror":"https://ror.org/02caytj08"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":40,"referenced_works":["https://openalex.org/W1525122828","https://openalex.org/W1968222033","https://openalex.org/W1968248603","https://openalex.org/W1973562367","https://openalex.org/W1978513278","https://openalex.org/W1984111577","https://openalex.org/W1985301978","https://openalex.org/W2007736465","https://openalex.org/W2007889263","https://openalex.org/W2021441691","https://openalex.org/W2032129634","https://openalex.org/W2044647456","https://openalex.org/W2046185660","https://openalex.org/W2046791391","https://openalex.org/W2050350880","https://openalex.org/W2075335828","https://openalex.org/W2089340783","https://openalex.org/W2093882245","https://openalex.org/W2097114111","https://openalex.org/W2099402486","https://openalex.org/W2099598643","https://openalex.org/W2110367525","https://openalex.org/W2127405865","https://openalex.org/W2130876515","https://openalex.org/W2133593582","https://openalex.org/W2134152126","https://openalex.org/W2136155687","https://openalex.org/W2151709132","https://openalex.org/W2207225738","https://openalex.org/W2254963963","https://openalex.org/W2258806502","https://openalex.org/W2307272104","https://openalex.org/W2323666809","https://openalex.org/W2338745262","https://openalex.org/W2507547280","https://openalex.org/W2520009198","https://openalex.org/W2743892428","https://openalex.org/W2755262660","https://openalex.org/W2952920983","https://openalex.org/W4256503849"],"related_works":["https://openalex.org/W4281719761","https://openalex.org/W2997716619","https://openalex.org/W2803565370","https://openalex.org/W3042135147","https://openalex.org/W4246210770","https://openalex.org/W2999946192","https://openalex.org/W4312018817","https://openalex.org/W2893616852","https://openalex.org/W4212814602","https://openalex.org/W4293249676"],"abstract_inverted_index":{"Abstract":[0],"We":[1],"report":[2],"a":[3,9,22,33],"site\u2010selective":[4],"cysteine\u2013cyclooctyne":[5],"conjugation":[6,50],"reaction":[7,45],"between":[8],"seven\u2010residue":[10],"peptide":[11,23,35,97],"tag":[12],"(DBCO\u2010tag,":[13],"Leu\u2010Cys\u2010Tyr\u2010Pro\u2010Trp\u2010Val\u2010Tyr)":[14],"at":[15],"the":[16,37,40,43,67,89],"N":[17],"or":[18,24],"C":[19],"terminus":[20],"of":[21,42,51,64,69],"protein":[25,68,87],"and":[26,59,88],"various":[27],"aza\u2010dibenzocyclooctyne":[28],"(DBCO)":[29],"reagents.":[30],"Compared":[31],"to":[32,53,109],"cysteine":[34,73],"control,":[36],"DBCO\u2010tag":[38,52,65],"increases":[39],"rate":[41],"thiol\u2013yne":[44],"220\u2010fold,":[46],"thereby":[47],"enabling":[48],"selective":[49],"DBCO\u2010linked":[54],"fluorescent":[55,86],"probes,":[56],"affinity":[57],"tags,":[58],"cytotoxic":[60],"drug":[61],"molecules.":[62],"Fusion":[63],"with":[66],"interest":[70],"enables":[71],"regioselective":[72],"modification":[74],"on":[75],"proteins":[76],"that":[77,95,105],"contain":[78],"multiple":[79],"endogenous":[80],"cysteines;":[81],"these":[82],"examples":[83],"include":[84],"green":[85],"antibody":[90],"trastuzumab.":[91],"This":[92],"study":[93],"demonstrates":[94],"short":[96],"tags":[98],"can":[99],"aid":[100],"in":[101,111],"accelerating":[102],"bond\u2010forming":[103],"reactions":[104],"are":[106],"often":[107],"slow":[108],"non\u2010existent":[110],"water.":[112]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":2},{"year":2020,"cited_by_count":6},{"year":2019,"cited_by_count":3}],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2020-01-30T00:00:00"}
