{"id":"https://openalex.org/W2117847277","doi":"https://doi.org/10.1111/j.1399-3011.2005.00241.x","title":"Preparation of protected peptidyl thioester intermediates for native chemical ligation by N\u03b1\u20109\u2010fluorenylmethoxycarbonyl (Fmoc) chemistry: considerations of side\u2010chain and backbone anchoring strategies, and compatible protection for N\u2010terminal cysteine*,\u2020","display_name":"Preparation of protected peptidyl thioester intermediates for native chemical ligation by N\u03b1\u20109\u2010fluorenylmethoxycarbonyl (Fmoc) chemistry: considerations of side\u2010chain and backbone anchoring strategies, and compatible protection for N\u2010terminal cysteine*,\u2020","publication_year":2005,"publication_date":"2005-03-01","ids":{"openalex":"https://openalex.org/W2117847277","doi":"https://doi.org/10.1111/j.1399-3011.2005.00241.x","mag":"2117847277","pmid":"https://pubmed.ncbi.nlm.nih.gov/15787970"},"language":"en","primary_location":{"id":"doi:10.1111/j.1399-3011.2005.00241.x","doi":"https://doi.org/10.1111/j.1399-3011.2005.00241.x","is_oa":false,"landing_page_url":"https://doi.org/10.1111/j.1399-3011.2005.00241.x","pdf_url":null,"source":{"id":"https://openalex.org/S122310368","display_name":"Journal of Peptide Research","issn_l":"1397-002X","issn":["1397-002X","1399-3011"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"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":"The Journal of Peptide Research","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/A5015845324","display_name":"Christopher M. Gross","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"C.M. Gross","raw_affiliation_strings":["Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA","institution_ids":["https://openalex.org/I130238516"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5072165376","display_name":"Dominique Leli\u00e8vre","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"D. Leli\u00e8vre","raw_affiliation_strings":["C.M. Gross, D. Lelie\u0300vre and G. Barany, Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA\nC.M. Gross and C.K. Woodward, Department of Biochemistry, Biophysics and Molecular Biology, University of Minnesota, St. Paul, MN 55108, USA","University of Minnesota, Minneapolis, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"C.M. Gross, D. Lelie\u0300vre and G. Barany, Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA\nC.M. Gross and C.K. Woodward, Department of Biochemistry, Biophysics and Molecular Biology, University of Minnesota, St. Paul, MN 55108, USA","institution_ids":["https://openalex.org/I130238516"]},{"raw_affiliation_string":"University of Minnesota, Minneapolis, United States","institution_ids":["https://openalex.org/I130238516"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5013399335","display_name":"Clare K. Woodward","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"C.K. Woodward","raw_affiliation_strings":["C.M. Gross, D. Lelie\u0300vre and G. Barany, Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA\nC.M. Gross and C.K. Woodward, Department of Biochemistry, Biophysics and Molecular Biology, University of Minnesota, St. Paul, MN 55108, USA","University of Minnesota, Minneapolis, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"C.M. Gross, D. Lelie\u0300vre and G. Barany, Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA\nC.M. Gross and C.K. Woodward, Department of Biochemistry, Biophysics and Molecular Biology, University of Minnesota, St. Paul, MN 55108, USA","institution_ids":["https://openalex.org/I130238516"]},{"raw_affiliation_string":"University of Minnesota, Minneapolis, United States","institution_ids":["https://openalex.org/I130238516"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5019782256","display_name":"George B\u00e1r\u00e1ny","orcid":"https://orcid.org/0000-0002-6373-2706","observed_orcids":["https://orcid.org/0000-0002-6373-2706"]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"G. Barany","raw_affiliation_strings":["C.M. Gross, D. Lelie\u0300vre and G. Barany, Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA\nC.M. Gross and C.K. Woodward, Department of Biochemistry, Biophysics and Molecular Biology, University of Minnesota, St. Paul, MN 55108, USA","University of Minnesota, Minneapolis, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"C.M. Gross, D. Lelie\u0300vre and G. Barany, Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA\nC.M. Gross and C.K. Woodward, Department of Biochemistry, Biophysics and Molecular Biology, University of Minnesota, St. Paul, MN 55108, USA","institution_ids":["https://openalex.org/I130238516"]},{"raw_affiliation_string":"University of Minnesota, Minneapolis, United States","institution_ids":["https://openalex.org/I130238516"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5019782256"],"corresponding_institution_ids":["https://openalex.org/I130238516"],"apc_list":null,"apc_paid":null,"fwci":1.3353,"has_fulltext":false,"cited_by_count":36,"citation_normalized_percentile":{"value":0.77074204,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"65","issue":"3","first_page":"395","last_page":"410"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":1.0,"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":1.0,"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/T13326","display_name":"Biochemical and Structural Characterization","score":0.0,"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/T10044","display_name":"Protein Structure and Dynamics","score":0.0,"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/native-chemical-ligation","display_name":"native chemical ligation","score":0.9909999966621399},{"id":"https://openalex.org/keywords/peptide-thioesters","display_name":"peptide thioesters","score":0.8149999976158142},{"id":"https://openalex.org/keywords/fmoc-chemistry","display_name":"Fmoc chemistry","score":0.9089999794960022},{"id":"https://openalex.org/keywords/n-terminal-cysteine","display_name":"N-terminal cysteine","score":0.7670000195503235},{"id":"https://openalex.org/keywords/aprotinin","display_name":"aprotinin","score":0.8240000009536743},{"id":"https://openalex.org/keywords/peptide-synthesis","display_name":"peptide synthesis","score":0.3580000102519989}],"concepts":[{"id":"https://openalex.org/C2778032875","wikidata":"https://www.wikidata.org/wiki/Q17152469","display_name":"Native chemical ligation","level":4,"score":0.954567015171051},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8003383874893188},{"id":"https://openalex.org/C162776295","wikidata":"https://www.wikidata.org/wiki/Q901154","display_name":"Semisynthesis","level":2,"score":0.7302309274673462},{"id":"https://openalex.org/C2779281246","wikidata":"https://www.wikidata.org/wiki/Q172847","display_name":"Peptide","level":2,"score":0.7206933498382568},{"id":"https://openalex.org/C2779201268","wikidata":"https://www.wikidata.org/wiki/Q186474","display_name":"Cysteine","level":3,"score":0.696126401424408},{"id":"https://openalex.org/C99207889","wikidata":"https://www.wikidata.org/wiki/Q5090481","display_name":"Chemical ligation","level":3,"score":0.6512534618377686},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6332862377166748},{"id":"https://openalex.org/C175156509","wikidata":"https://www.wikidata.org/wiki/Q1990218","display_name":"Cleavage (geology)","level":3,"score":0.6090112924575806},{"id":"https://openalex.org/C204921945","wikidata":"https://www.wikidata.org/wiki/Q899689","display_name":"Side chain","level":3,"score":0.6089729070663452},{"id":"https://openalex.org/C2780340462","wikidata":"https://www.wikidata.org/wiki/Q127450","display_name":"Trypsin","level":3,"score":0.4452567398548126},{"id":"https://openalex.org/C2778834346","wikidata":"https://www.wikidata.org/wiki/Q422794","display_name":"Thioester","level":3,"score":0.43864360451698303},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4172394871711731},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.27288469672203064},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.18735387921333313},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.07027298212051392},{"id":"https://openalex.org/C127413603","wikidata":"https://www.wikidata.org/wiki/Q11023","display_name":"Engineering","level":0,"score":0.0},{"id":"https://openalex.org/C521977710","wikidata":"https://www.wikidata.org/wiki/Q81163","display_name":"Polymer","level":2,"score":0.0},{"id":"https://openalex.org/C187320778","wikidata":"https://www.wikidata.org/wiki/Q1349130","display_name":"Geotechnical engineering","level":1,"score":0.0},{"id":"https://openalex.org/C43369102","wikidata":"https://www.wikidata.org/wiki/Q2307625","display_name":"Fracture (geology)","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000595","descriptor_name":"Amino Acid Sequence","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000596","descriptor_name":"Amino Acids","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000596","descriptor_name":"Amino Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D003545","descriptor_name":"Cysteine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D005449","descriptor_name":"Fluorenes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D005449","descriptor_name":"Fluorenes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D007611","descriptor_name":"Aprotinin","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D007611","descriptor_name":"Aprotinin","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D008969","descriptor_name":"Molecular Sequence Data","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010446","descriptor_name":"Peptide Fragments","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D010446","descriptor_name":"Peptide Fragments","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013457","descriptor_name":"Sulfur Compounds","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D013457","descriptor_name":"Sulfur Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1111/j.1399-3011.2005.00241.x","doi":"https://doi.org/10.1111/j.1399-3011.2005.00241.x","is_oa":false,"landing_page_url":"https://doi.org/10.1111/j.1399-3011.2005.00241.x","pdf_url":null,"source":{"id":"https://openalex.org/S122310368","display_name":"Journal of Peptide Research","issn_l":"1397-002X","issn":["1397-002X","1399-3011"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"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":"The Journal of Peptide Research","raw_type":"journal-article"},{"id":"pmid:15787970","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15787970","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":"The journal of peptide research : official journal of the American Peptide Society","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":68,"referenced_works":["https://openalex.org/W42476878","https://openalex.org/W104821597","https://openalex.org/W1483590021","https://openalex.org/W1509586536","https://openalex.org/W1516367946","https://openalex.org/W1539245352","https://openalex.org/W1566789051","https://openalex.org/W1607748786","https://openalex.org/W1967975735","https://openalex.org/W1969848980","https://openalex.org/W1974957051","https://openalex.org/W1976897275","https://openalex.org/W1980263071","https://openalex.org/W1984574571","https://openalex.org/W1987063175","https://openalex.org/W1989137186","https://openalex.org/W1990332976","https://openalex.org/W1992424014","https://openalex.org/W1994165491","https://openalex.org/W1995380081","https://openalex.org/W1997173055","https://openalex.org/W1998287079","https://openalex.org/W2002480858","https://openalex.org/W2007747833","https://openalex.org/W2009039916","https://openalex.org/W2010954863","https://openalex.org/W2011901435","https://openalex.org/W2016478728","https://openalex.org/W2021293377","https://openalex.org/W2023319785","https://openalex.org/W2026090217","https://openalex.org/W2027163628","https://openalex.org/W2028947145","https://openalex.org/W2030755527","https://openalex.org/W2030863777","https://openalex.org/W2031544977","https://openalex.org/W2034817631","https://openalex.org/W2036393228","https://openalex.org/W2037387279","https://openalex.org/W2038561031","https://openalex.org/W2038701763","https://openalex.org/W2045765602","https://openalex.org/W2048258234","https://openalex.org/W2055702409","https://openalex.org/W2058230014","https://openalex.org/W2068303796","https://openalex.org/W2068523347","https://openalex.org/W2068740346","https://openalex.org/W2070885678","https://openalex.org/W2077780326","https://openalex.org/W2081667785","https://openalex.org/W2081745201","https://openalex.org/W2082022880","https://openalex.org/W2083610655","https://openalex.org/W2084311171","https://openalex.org/W2084631067","https://openalex.org/W2084674494","https://openalex.org/W2089128504","https://openalex.org/W2137250659","https://openalex.org/W2138995597","https://openalex.org/W2148405034","https://openalex.org/W2166405062","https://openalex.org/W2415894594","https://openalex.org/W2486200327","https://openalex.org/W2920822596","https://openalex.org/W3021626239","https://openalex.org/W4213262935","https://openalex.org/W4242910826"],"related_works":["https://openalex.org/W3031414425","https://openalex.org/W1995380081","https://openalex.org/W2054012870","https://openalex.org/W2276391291","https://openalex.org/W3009150325","https://openalex.org/W7051954433","https://openalex.org/W2415894594","https://openalex.org/W2007708133","https://openalex.org/W2059912289","https://openalex.org/W2122498131"],"abstract_inverted_index":{"Native":[0],"chemical":[1,186],"ligation":[2,65],"has":[3],"proven":[4],"to":[5,47,54,63,82,181],"be":[6],"a":[7,139,152],"powerful":[8],"method":[9],"for":[10,105],"the":[11,17,33,71,84,94,107,167,182],"synthesis":[12],"of":[13,19,38,96,117,122,135,148,160],"small":[14],"proteins":[15],"and":[16,59,75,145,172],"semisynthesis":[18],"larger":[20],"ones.":[21],"The":[22],"essential":[23],"synthetic":[24],"intermediates,":[25],"which":[26],"are":[27,164],"C-terminal":[28],"peptide":[29,43,91],"thioesters,":[30],"cannot":[31],"survive":[32],"repetitive":[34],"piperidine":[35],"deprotection":[36,171],"steps":[37,174],"N(alpha)-9-fluorenylmethoxycarbonyl":[39],"(Fmoc)":[40],"chemistry.":[41,69],"Therefore,":[42],"scientists":[44],"who":[45],"prefer":[46],"not":[48],"use":[49],"N(alpha)-t-butyloxycarbonyl":[50],"(Boc)":[51],"chemistry":[52],"need":[53],"adopt":[55],"more":[56],"esoteric":[57],"strategies":[58,78,104],"tactics":[60],"in":[61,195],"order":[62],"integrate":[64],"approaches":[66],"with":[67,129],"Fmoc":[68],"In":[70,157],"present":[72],"work,":[73],"side-chain":[74],"backbone":[76],"anchoring":[77],"have":[79,112],"been":[80,113],"used":[81],"prepare":[83],"required":[85],"suitably":[86],"(partially)":[87],"protected":[88,126],"and/or":[89],"activated":[90],"intermediates":[92],"spanning":[93],"length":[95],"bovine":[97],"pancreatic":[98],"trypsin":[99],"inhibitor":[100],"(BPTI).":[101],"Three":[102],"separate":[103,158],"managing":[106],"critical":[108],"N-terminal":[109,130],"cysteine":[110],"residue":[111],"developed:":[114],"(i)":[115],"incorporation":[116,134,147],"N(alpha)-9-fluorenylmethoxycarbonyl-S-(N-methyl-N-phenylcarbamoyl)sulfenylcysteine":[118],"[Fmoc-Cys(Snm)-OH],":[119],"allowing":[120],"creation":[121],"an":[123],"otherwise":[124],"fully":[125],"resin-bound":[127],"intermediate":[128],"free":[131],"Cys;":[132],"(ii)":[133],"N(alpha)-9-fluorenylmethoxycarbonyl-S-triphenylmethylcysteine":[136],"[Fmoc-Cys(Trt)-OH],":[137],"generating":[138,151],"stable":[140,153],"Fmoc-Cys(H)-peptide":[141],"upon":[142,155],"acidolytic":[143],"cleavage;":[144],"(iii)":[146],"N(alpha)-t-butyloxycarbonyl-S-fluorenylmethylcysteine":[149],"[Boc-Cys(Fm)-OH],":[150],"H-Cys(Fm)-peptide":[154],"cleavage.":[156],"stages":[159],"these":[161],"strategies,":[162],"thioesters":[163],"established":[165],"at":[166],"C-termini":[168],"by":[169],"selective":[170],"coupling":[173],"carried":[175],"out":[176],"while":[177],"peptides":[178],"remain":[179],"bound":[180],"supports.":[183],"Pilot":[184],"native":[185],"ligations":[187],"were":[188],"pursued":[189],"directly":[190],"on-resin,":[191],"as":[192,194],"well":[193],"solution":[196],"after":[197],"cleavage/purification.":[198]},"counts_by_year":[{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":3},{"year":2012,"cited_by_count":2}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
