{"id":"https://openalex.org/W3082390959","doi":"https://doi.org/10.1002/chem.202003548","title":"A Peptide Stapling Strategy with Built\u2010In Fluorescence by Direct Late\u2010Stage C(sp2)\u2212H Olefination of Tryptophan","display_name":"A Peptide Stapling Strategy with Built\u2010In Fluorescence by Direct Late\u2010Stage C(sp2)\u2212H Olefination of Tryptophan","publication_year":2020,"publication_date":"2020-08-31","ids":{"openalex":"https://openalex.org/W3082390959","doi":"https://doi.org/10.1002/chem.202003548","mag":"3082390959","pmid":"https://pubmed.ncbi.nlm.nih.gov/32864789"},"language":"en","primary_location":{"id":"doi:10.1002/chem.202003548","doi":"https://doi.org/10.1002/chem.202003548","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.202003548","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"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":"Chemistry \u2013 A European Journal","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"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/A5100325228","display_name":"Jiang Liu","orcid":"https://orcid.org/0000-0002-5336-7354","observed_orcids":["https://orcid.org/0000-0002-5336-7354"]},"institutions":[{"id":"https://openalex.org/I55712492","display_name":"Zhejiang University of Technology","ror":"https://ror.org/02djqfd08","country_code":"CN","type":"education","lineage":["https://openalex.org/I55712492"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Jiang Liu","raw_affiliation_strings":["Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China","institution_ids":["https://openalex.org/I55712492"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5101552812","display_name":"Xin Liu","orcid":"https://orcid.org/0009-0009-5427-9370","observed_orcids":["https://orcid.org/0009-0009-5427-9370"]},"institutions":[{"id":"https://openalex.org/I55712492","display_name":"Zhejiang University of Technology","ror":"https://ror.org/02djqfd08","country_code":"CN","type":"education","lineage":["https://openalex.org/I55712492"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Xin Liu","raw_affiliation_strings":["Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China","institution_ids":["https://openalex.org/I55712492"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100425801","display_name":"Fangfang Zhang","orcid":"https://orcid.org/0000-0001-6450-5129","observed_orcids":["https://orcid.org/0000-0001-6450-5129"]},"institutions":[{"id":"https://openalex.org/I55712492","display_name":"Zhejiang University of Technology","ror":"https://ror.org/02djqfd08","country_code":"CN","type":"education","lineage":["https://openalex.org/I55712492"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Fangfang Zhang","raw_affiliation_strings":["Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China","institution_ids":["https://openalex.org/I55712492"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5041418037","display_name":"Jiaojiao Qu","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I55712492","display_name":"Zhejiang University of Technology","ror":"https://ror.org/02djqfd08","country_code":"CN","type":"education","lineage":["https://openalex.org/I55712492"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Jiaojiao Qu","raw_affiliation_strings":["Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China","institution_ids":["https://openalex.org/I55712492"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5060604363","display_name":"Hongyan Sun","orcid":"https://orcid.org/0000-0003-0932-6405","observed_orcids":["https://orcid.org/0000-0003-0932-6405"]},"institutions":[{"id":"https://openalex.org/I168719708","display_name":"City University of Hong Kong","ror":"https://ror.org/03q8dnn23","country_code":"HK","type":"education","lineage":["https://openalex.org/I168719708"]}],"countries":["HK"],"is_corresponding":false,"raw_author_name":"Hongyan Sun","raw_affiliation_strings":["Department of Chemistry and Center of Super-Diamond and Advanced Films (COSDAF), City University of Hong Kong, Hong Kong, P.R. China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Center of Super-Diamond and Advanced Films (COSDAF), City University of Hong Kong, Hong Kong, P.R. China","institution_ids":["https://openalex.org/I168719708"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5006549974","display_name":"Qing xia Zhu","orcid":"https://orcid.org/0000-0002-0761-9434","observed_orcids":["https://orcid.org/0000-0002-0761-9434"]},"institutions":[{"id":"https://openalex.org/I55712492","display_name":"Zhejiang University of Technology","ror":"https://ror.org/02djqfd08","country_code":"CN","type":"education","lineage":["https://openalex.org/I55712492"]}],"countries":["CN"],"is_corresponding":true,"raw_author_name":"Qing Zhu","raw_affiliation_strings":["Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China"],"raw_orcid":"https://orcid.org/0000-0002-0761-9434","affiliations":[{"raw_affiliation_string":"Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P.R. China","institution_ids":["https://openalex.org/I55712492"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5006549974"],"corresponding_institution_ids":["https://openalex.org/I55712492"],"apc_list":{"value":4000,"currency":"USD","value_usd":4000},"apc_paid":null,"fwci":1.208,"has_fulltext":false,"cited_by_count":32,"citation_normalized_percentile":{"value":0.73080974,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"26","issue":"68","first_page":"16122","last_page":"16128"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.8657000064849854,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.8657000064849854,"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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.05339999869465828,"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/T11440","display_name":"Click Chemistry and Applications","score":0.023000000044703484,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/peptide-stapling","display_name":"peptide stapling","score":0.7649999856948853},{"id":"https://openalex.org/keywords/tryptophan","display_name":"tryptophan","score":0.8539999723434448},{"id":"https://openalex.org/keywords/rhodium-catalysis","display_name":"rhodium catalysis","score":0.9810000061988831},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.7200000286102295},{"id":"https://openalex.org/keywords/integrin-alphavbeta3","display_name":"integrin \u03b1v\u03b23","score":0.859000027179718},{"id":"https://openalex.org/keywords/cellular-imaging","display_name":"cell imaging","score":0.7599999904632568},{"id":"https://openalex.org/keywords/anticancer-activity","display_name":"anticancer activity","score":0.843999981880188},{"id":"https://openalex.org/keywords/cyclic-rgd-peptide","display_name":"cyclic RGD peptide","score":0.6079999804496765},{"id":"https://openalex.org/keywords/peptide-macrocyclization","display_name":"peptide macrocyclization","score":0.9490000009536743}],"concepts":[{"id":"https://openalex.org/C2778617687","wikidata":"https://www.wikidata.org/wiki/Q2448456","display_name":"Fluorophore","level":3,"score":0.7676585912704468},{"id":"https://openalex.org/C2779281246","wikidata":"https://www.wikidata.org/wiki/Q172847","display_name":"Peptide","level":2,"score":0.7663679122924805},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7287399768829346},{"id":"https://openalex.org/C2776706248","wikidata":"https://www.wikidata.org/wiki/Q181003","display_name":"Tryptophan","level":3,"score":0.6792134046554565},{"id":"https://openalex.org/C91881484","wikidata":"https://www.wikidata.org/wiki/Q191807","display_name":"Fluorescence","level":2,"score":0.6489618420600891},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.5264813899993896},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.500882625579834},{"id":"https://openalex.org/C60984968","wikidata":"https://www.wikidata.org/wiki/Q389172","display_name":"Cyclic peptide","level":3,"score":0.48143312335014343},{"id":"https://openalex.org/C2779485729","wikidata":"https://www.wikidata.org/wiki/Q210385","display_name":"Pyridine","level":2,"score":0.452910453081131},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.40786442160606384},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.40440109372138977},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.3097892999649048},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.10729095339775085},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.09975063800811768},{"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/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000072283","descriptor_name":"A549 Cells","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005453","descriptor_name":"Fluorescence","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005456","descriptor_name":"Fluorescent Dyes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010455","descriptor_name":"Peptides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D012238","descriptor_name":"Rhodium","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D014364","descriptor_name":"Tryptophan","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D039302","descriptor_name":"Integrin alphaVbeta3","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1002/chem.202003548","doi":"https://doi.org/10.1002/chem.202003548","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.202003548","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"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":"Chemistry \u2013 A European Journal","raw_type":"journal-article"},{"id":"pmid:32864789","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/32864789","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry (Weinheim an der Bergstrasse, Germany)","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1144668291","display_name":"\u57fa\u4e8e\u6d3b\u6027\u5c0f\u5206\u5b50\u63a2\u9488\u7684\u539f\u53d1\u6027\u809d\u764c\u7ec4\u7ec7\u5185\u86cb\u767d\u9176\u8868\u8fbe\u8c31\u7684\u7814\u7a76","funder_award_id":"21472172","funder_id":"https://openalex.org/F4320321001","funder_display_name":"National Natural Science Foundation of China"},{"id":"https://openalex.org/G2493777781","display_name":"\u65b0\u578b\u8fd1\u7ea2\u5916\u6c34\u89e3\u9176FRET\u63a2\u9488\u8bbe\u8ba1\u3001\u5236\u5907\u53ca\u53ef\u89c6\u5316\u7814\u7a76","funder_award_id":"21272212","funder_id":"https://openalex.org/F4320321001","funder_display_name":"National Natural Science Foundation of China"}],"funders":[{"id":"https://openalex.org/F4320321001","display_name":"National Natural Science Foundation of China","ror":"https://ror.org/01h0zpd94"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":55,"referenced_works":["https://openalex.org/W12071157","https://openalex.org/W1875439262","https://openalex.org/W1981562300","https://openalex.org/W1984701286","https://openalex.org/W1985190876","https://openalex.org/W2008080581","https://openalex.org/W2015423441","https://openalex.org/W2092474693","https://openalex.org/W2099404272","https://openalex.org/W2126907199","https://openalex.org/W2150084524","https://openalex.org/W2156310621","https://openalex.org/W2158065054","https://openalex.org/W2197514493","https://openalex.org/W2263462535","https://openalex.org/W2276210017","https://openalex.org/W2296564964","https://openalex.org/W2418613249","https://openalex.org/W2492077723","https://openalex.org/W2529969786","https://openalex.org/W2553503323","https://openalex.org/W2557747788","https://openalex.org/W2567594059","https://openalex.org/W2569303361","https://openalex.org/W2587649655","https://openalex.org/W2606011273","https://openalex.org/W2620137284","https://openalex.org/W2786104270","https://openalex.org/W2789678879","https://openalex.org/W2794590245","https://openalex.org/W2886179501","https://openalex.org/W2889102387","https://openalex.org/W2892586100","https://openalex.org/W2901437621","https://openalex.org/W2902780231","https://openalex.org/W2903385757","https://openalex.org/W2921762974","https://openalex.org/W2928141543","https://openalex.org/W2949710511","https://openalex.org/W2968778599","https://openalex.org/W2975706162","https://openalex.org/W2982331182","https://openalex.org/W2986303123","https://openalex.org/W2998713732","https://openalex.org/W3012245774","https://openalex.org/W3025545781","https://openalex.org/W3033054887","https://openalex.org/W4212883317","https://openalex.org/W4230453782","https://openalex.org/W4234442147","https://openalex.org/W4244718249","https://openalex.org/W4251349471","https://openalex.org/W4253701173","https://openalex.org/W6683460682","https://openalex.org/W6776757370"],"related_works":["https://openalex.org/W3025545781","https://openalex.org/W2772475198","https://openalex.org/W4404083195","https://openalex.org/W4200124471","https://openalex.org/W4225767184","https://openalex.org/W2263462535","https://openalex.org/W4392359854","https://openalex.org/W4383093212","https://openalex.org/W4382678671","https://openalex.org/W4405248849"],"abstract_inverted_index":{"Abstract":[0],"Fluorescent":[1],"stapled":[2,52,58,98],"peptides":[3,20,53,59,99,116],"are":[4,21],"important":[5],"chemical":[6],"tools":[7,148],"for":[8,49,94,110,149],"detecting":[9],"intracellular":[10],"distribution,":[11],"protein\u2013protein":[12],"interactions,":[13],"and":[14,38,85,105],"localization":[15],"of":[16,41,92],"target":[17],"proteins.":[18],"These":[19,115],"usually":[22],"labeled":[23],"with":[24,54],"bulky":[25],"sized":[26],"fluorophores":[27],"through":[28,62],"reactive":[29],"functional":[30],"groups,":[31],"which":[32],"may":[33],"alter":[34],"the":[35,74,150],"physical":[36],"properties":[37],"biological":[39,96],"activities":[40],"peptides.":[42],"Herein,":[43],"a":[44,90,104,111],"unique":[45],"strategy":[46],"is":[47],"developed":[48],"synthesizing":[50],"new":[51],"built\u2010in":[55],"fluorescence.":[56],"The":[57,143],"were":[60,108],"prepared":[61],"Rh\u2010catalyzed":[63],"C(sp2)\u2212H":[64],"olefination":[65],"in":[66,124],"tryptophan":[67],"(Trp)":[68],"residues":[69],"by":[70,127],"using":[71],"pyridine/pyrimidine":[72],"as":[73,89],"directing":[75],"groups":[76],"under":[77],"mild":[78],"conditions.":[79],"This":[80],"method":[81,144],"displays":[82],"good":[83],"regioselectivity":[84],"high":[86],"efficiency.":[87],"Furthermore,":[88],"proof":[91],"concept":[93],"its":[95],"applications,":[97],"without":[100],"additional":[101],"fluorophore":[102],"9":[103,106],"b":[107],"constructed":[109],"cell":[112,128],"imaging":[113,129],"study.":[114],"displayed":[117],"strong":[118],"binding":[119],"affinity":[120],"toward":[121],"integrin":[122],"\u03b1v\u03b23":[123],"A549":[125],"cells":[126],"experiments.":[130],"Notably":[131],"they":[132],"demonstrated":[133],"even":[134],"better":[135],"anticancer":[136],"activity":[137],"than":[138],"commercial":[139],"antagonist":[140],"cyclic":[141],"(RGDfK).":[142],"will":[145],"provide":[146],"robust":[147],"peptide":[151],"macrocyclization":[152],"field.":[153]},"counts_by_year":[{"year":2026,"cited_by_count":6},{"year":2025,"cited_by_count":9},{"year":2024,"cited_by_count":4},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":3},{"year":2021,"cited_by_count":4},{"year":2020,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2020-09-08T00:00:00"}