{"id":"https://openalex.org/W2467612923","doi":"https://doi.org/10.1039/c6ob01159d","title":"A mechanistic study on the inhibition of \u03b1-chymotrypsin by a macrocyclic peptidomimetic aldehyde","display_name":"A mechanistic study on the inhibition of \u03b1-chymotrypsin by a macrocyclic peptidomimetic aldehyde","publication_year":2016,"publication_date":"2016-01-01","ids":{"openalex":"https://openalex.org/W2467612923","doi":"https://doi.org/10.1039/c6ob01159d","mag":"2467612923","pmid":"https://pubmed.ncbi.nlm.nih.gov/27349772"},"language":"en","primary_location":{"id":"doi:10.1039/c6ob01159d","doi":"https://doi.org/10.1039/c6ob01159d","is_oa":false,"landing_page_url":"https://doi.org/10.1039/c6ob01159d","pdf_url":null,"source":{"id":"https://openalex.org/S179810352","display_name":"Organic & Biomolecular Chemistry","issn_l":"1477-0520","issn":["1477-0520","1477-0539"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-2","ki-jl-1","medline","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic & Biomolecular Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","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/A5077409842","display_name":"Xiaoli Zhang","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4391768102","display_name":"ARC Centre for Nanoscale BioPhotonics","ror":"https://ror.org/00g76w893","country_code":"AU","type":"facility","lineage":["https://openalex.org/I4391768102"]},{"id":"https://openalex.org/I5681781","display_name":"The University of Adelaide","ror":"https://ror.org/00892tw58","country_code":"AU","type":"education","lineage":["https://openalex.org/I4405259444","https://openalex.org/I5681781"]}],"countries":["AU"],"is_corresponding":false,"raw_author_name":"X. Zhang","raw_affiliation_strings":["ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP)","Adelaide","Department of Chemistry","Institute for Photonics and Advanced Sensing","The University of Adelaide","ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP), Institute for Photonics and Advanced Sensing, Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia","Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP)","institution_ids":["https://openalex.org/I4391768102"]},{"raw_affiliation_string":"Adelaide","institution_ids":[]},{"raw_affiliation_string":"Department of Chemistry","institution_ids":[]},{"raw_affiliation_string":"Institute for Photonics and Advanced Sensing","institution_ids":[]},{"raw_affiliation_string":"The University of Adelaide","institution_ids":["https://openalex.org/I5681781"]},{"raw_affiliation_string":"ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP), Institute for Photonics and Advanced Sensing, Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia","institution_ids":["https://openalex.org/I4391768102","https://openalex.org/I5681781"]},{"raw_affiliation_string":"Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia","institution_ids":["https://openalex.org/I5681781"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5059039218","display_name":"John B. Bruning","orcid":"https://orcid.org/0000-0002-6919-1824","observed_orcids":["https://orcid.org/0000-0002-6919-1824"]},"institutions":[{"id":"https://openalex.org/I5681781","display_name":"The University of Adelaide","ror":"https://ror.org/00892tw58","country_code":"AU","type":"education","lineage":["https://openalex.org/I4405259444","https://openalex.org/I5681781"]}],"countries":["AU"],"is_corresponding":false,"raw_author_name":"J. B. Bruning","raw_affiliation_strings":["Adelaide","Australia","School of Biological Sciences","The University of Adelaide","School of Biological Sciences, The University of Adelaide, Adelaide, SA 5005, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Adelaide","institution_ids":[]},{"raw_affiliation_string":"Australia","institution_ids":[]},{"raw_affiliation_string":"School of Biological Sciences","institution_ids":[]},{"raw_affiliation_string":"The University of Adelaide","institution_ids":["https://openalex.org/I5681781"]},{"raw_affiliation_string":"School of Biological Sciences, The University of Adelaide, Adelaide, SA 5005, Australia","institution_ids":["https://openalex.org/I5681781"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5080675508","display_name":"Jonathan H. George","orcid":"https://orcid.org/0000-0002-7330-2160","observed_orcids":["https://orcid.org/0000-0002-7330-2160"]},"institutions":[{"id":"https://openalex.org/I5681781","display_name":"The University of Adelaide","ror":"https://ror.org/00892tw58","country_code":"AU","type":"education","lineage":["https://openalex.org/I4405259444","https://openalex.org/I5681781"]}],"countries":["AU"],"is_corresponding":false,"raw_author_name":"J. H. George","raw_affiliation_strings":["Adelaide","Australia","Department of Chemistry","The University of Adelaide","Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Adelaide","institution_ids":[]},{"raw_affiliation_string":"Australia","institution_ids":[]},{"raw_affiliation_string":"Department of Chemistry","institution_ids":[]},{"raw_affiliation_string":"The University of Adelaide","institution_ids":["https://openalex.org/I5681781"]},{"raw_affiliation_string":"Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia","institution_ids":["https://openalex.org/I5681781"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5033537928","display_name":"Andrew David Abell","orcid":"https://orcid.org/0000-0002-0604-2629","observed_orcids":["https://orcid.org/0000-0002-0604-2629"]},"institutions":[{"id":"https://openalex.org/I4391768102","display_name":"ARC Centre for Nanoscale BioPhotonics","ror":"https://ror.org/00g76w893","country_code":"AU","type":"facility","lineage":["https://openalex.org/I4391768102"]},{"id":"https://openalex.org/I5681781","display_name":"The University of Adelaide","ror":"https://ror.org/00892tw58","country_code":"AU","type":"education","lineage":["https://openalex.org/I4405259444","https://openalex.org/I5681781"]}],"countries":["AU"],"is_corresponding":true,"raw_author_name":"A. D. Abell","raw_affiliation_strings":["ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP)","Adelaide","Department of Chemistry","Institute for Photonics and Advanced Sensing","The University of Adelaide","ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP), Institute for Photonics and Advanced Sensing, Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia","Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP)","institution_ids":["https://openalex.org/I4391768102"]},{"raw_affiliation_string":"Adelaide","institution_ids":[]},{"raw_affiliation_string":"Department of Chemistry","institution_ids":[]},{"raw_affiliation_string":"Institute for Photonics and Advanced Sensing","institution_ids":[]},{"raw_affiliation_string":"The University of Adelaide","institution_ids":["https://openalex.org/I5681781"]},{"raw_affiliation_string":"ARC Centre of Excellence for Nanoscale BioPhotonics (CNBP), Institute for Photonics and Advanced Sensing, Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia","institution_ids":["https://openalex.org/I4391768102","https://openalex.org/I5681781"]},{"raw_affiliation_string":"Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia","institution_ids":["https://openalex.org/I5681781"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5033537928"],"corresponding_institution_ids":["https://openalex.org/I4391768102","https://openalex.org/I5681781"],"apc_list":null,"apc_paid":null,"fwci":0.9733,"has_fulltext":false,"cited_by_count":13,"citation_normalized_percentile":{"value":0.73458397,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":97},"biblio":{"volume":"14","issue":"29","first_page":"6970","last_page":"6978"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10620","display_name":"Protease and Inhibitor Mechanisms","score":0.4950999915599823,"subfield":{"id":"https://openalex.org/subfields/1306","display_name":"Cancer Research"},"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"}},"topics":[{"id":"https://openalex.org/T10620","display_name":"Protease and Inhibitor Mechanisms","score":0.4950999915599823,"subfield":{"id":"https://openalex.org/subfields/1306","display_name":"Cancer Research"},"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.45089998841285706,"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/T12191","display_name":"Chemical Reaction Mechanisms","score":0.008899999782443047,"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/alpha-chymotrypsin","display_name":"alpha-chymotrypsin","score":0.9829999804496765},{"id":"https://openalex.org/keywords/enzyme-inhibition","display_name":"enzyme inhibition","score":0.8029999732971191},{"id":"https://openalex.org/keywords/hemiacetal-intermediate","display_name":"hemiacetal intermediate","score":0.8579999804496765},{"id":"https://openalex.org/keywords/oxyanion-hole","display_name":"oxyanion hole","score":0.6800000071525574},{"id":"https://openalex.org/keywords/s1-subsite","display_name":"S1 subsite","score":0.9430000185966492},{"id":"https://openalex.org/keywords/hydrogen-bonding","display_name":"hydrogen bonding","score":0.8500000238418579},{"id":"https://openalex.org/keywords/beta-strand-conformation","display_name":"beta-strand conformation","score":0.8330000042915344},{"id":"https://openalex.org/keywords/crystal-structure","display_name":"crystal structure","score":0.47099998593330383}],"concepts":[{"id":"https://openalex.org/C124790011","wikidata":"https://www.wikidata.org/wiki/Q2069797","display_name":"Peptidomimetic","level":3,"score":0.9815595149993896},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9539874792098999},{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.8073013424873352},{"id":"https://openalex.org/C2778401398","wikidata":"https://www.wikidata.org/wiki/Q383836","display_name":"Chymotrypsin","level":4,"score":0.7657519578933716},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5291966199874878},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.5102574825286865},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.26356810331344604},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.25997185707092285},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.20483478903770447},{"id":"https://openalex.org/C2780340462","wikidata":"https://www.wikidata.org/wiki/Q127450","display_name":"Trypsin","level":3,"score":0.12770548462867737},{"id":"https://openalex.org/C2779281246","wikidata":"https://www.wikidata.org/wiki/Q172847","display_name":"Peptide","level":2,"score":0.07593858242034912},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.06711083650588989}],"mesh":[{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002918","descriptor_name":"Chymotrypsin","qualifier_ui":"Q000037","qualifier_name":"antagonists & inhibitors","is_major_topic":true},{"descriptor_ui":"D004791","descriptor_name":"Enzyme Inhibitors","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D004791","descriptor_name":"Enzyme Inhibitors","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D004791","descriptor_name":"Enzyme Inhibitors","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D008958","descriptor_name":"Models, Molecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D018360","descriptor_name":"Crystallography, X-Ray","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D047028","descriptor_name":"Macrocyclic Compounds","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D047028","descriptor_name":"Macrocyclic Compounds","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D047028","descriptor_name":"Macrocyclic Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D057786","descriptor_name":"Peptidomimetics","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D057786","descriptor_name":"Peptidomimetics","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":true},{"descriptor_ui":"D057786","descriptor_name":"Peptidomimetics","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1039/c6ob01159d","doi":"https://doi.org/10.1039/c6ob01159d","is_oa":false,"landing_page_url":"https://doi.org/10.1039/c6ob01159d","pdf_url":null,"source":{"id":"https://openalex.org/S179810352","display_name":"Organic & Biomolecular Chemistry","issn_l":"1477-0520","issn":["1477-0520","1477-0539"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-2","ki-jl-1","medline","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic & Biomolecular Chemistry","raw_type":"journal-article"},{"id":"pmid:27349772","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/27349772","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":"Organic & biomolecular chemistry","raw_type":"Journal Article"},{"id":"pmh:oai:digital.library.adelaide.edu.au:2440/101279","doi":null,"is_oa":false,"landing_page_url":"http://hdl.handle.net/2440/101279","pdf_url":null,"source":{"id":"https://openalex.org/S4306401835","display_name":"Adelaide Research & Scholarship (AR&S) (University of Adelaide)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I5681781","host_organization_name":"The University of Adelaide","host_organization_lineage":["https://openalex.org/I5681781"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"https://doi.org/10.1039/c6ob01159d","raw_type":"Journal article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320334704","display_name":"Australian Research Council","ror":"https://ror.org/05mmh0f86"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":47,"referenced_works":["https://openalex.org/W1876443773","https://openalex.org/W1965605636","https://openalex.org/W1982163944","https://openalex.org/W1984926832","https://openalex.org/W1985469117","https://openalex.org/W1992978957","https://openalex.org/W1996325896","https://openalex.org/W1998233841","https://openalex.org/W2000361762","https://openalex.org/W2002249897","https://openalex.org/W2004417740","https://openalex.org/W2008781418","https://openalex.org/W2032921692","https://openalex.org/W2033131456","https://openalex.org/W2051827977","https://openalex.org/W2052696994","https://openalex.org/W2057563075","https://openalex.org/W2059262179","https://openalex.org/W2060879531","https://openalex.org/W2063768610","https://openalex.org/W2066395642","https://openalex.org/W2066657190","https://openalex.org/W2067937943","https://openalex.org/W2070348389","https://openalex.org/W2070713982","https://openalex.org/W2072249390","https://openalex.org/W2072756383","https://openalex.org/W2085044850","https://openalex.org/W2091026598","https://openalex.org/W2096948978","https://openalex.org/W2105641709","https://openalex.org/W2111221356","https://openalex.org/W2115099305","https://openalex.org/W2117194232","https://openalex.org/W2126267349","https://openalex.org/W2131046434","https://openalex.org/W2140688181","https://openalex.org/W2142684817","https://openalex.org/W2155036500","https://openalex.org/W2165307962","https://openalex.org/W2171915460","https://openalex.org/W2182398922","https://openalex.org/W2246928826","https://openalex.org/W2321378571","https://openalex.org/W2484910684","https://openalex.org/W2505553904","https://openalex.org/W3005448147"],"related_works":["https://openalex.org/W6966642786","https://openalex.org/W2066783718","https://openalex.org/W2903648291","https://openalex.org/W2041182604","https://openalex.org/W2089771620","https://openalex.org/W2154988937","https://openalex.org/W2522883865","https://openalex.org/W2031992601","https://openalex.org/W2037850160","https://openalex.org/W2143767610"],"abstract_inverted_index":{"Here":[0],"we":[1],"describe":[2],"an":[3,51],"NMR":[4,36],"and":[5,33,86],"X-ray":[6,52],"crystallography-based":[7],"characterisation":[8],"of":[9,17,28,41,50],"the":[10,29,61,79,83],"mechanism":[11],"by":[12,76],"which":[13],"a":[14,25,42,64],"new":[15],"class":[16],"macrocyclic":[18],"peptidomimetic":[19],"aldehyde":[20],"inhibits":[21],"\u03b1-chymotrypsin.":[22,48],"In":[23],"particular,":[24],"(13)C-labelled":[26],"analogue":[27],"inhibitor":[30],"was":[31],"prepared":[32],"used":[34],"in":[35,55],"experiments":[37],"to":[38],"confirm":[39],"formation":[40],"hemiacetal":[43],"intermediate":[44],"on":[45],"binding":[46],"with":[47,57,78],"Analysis":[49],"crystallographic":[53],"structure":[54],"complex":[56],"\u03b1-chymotrypsin":[58],"reveals":[59],"that":[60],"backbone":[62],"adopts":[63],"stable":[65],"\u03b2-strand":[66],"conformation":[67],"as":[68],"per":[69],"its":[70],"design.":[71],"Binding":[72],"is":[73],"further":[74],"stabilised":[75],"interaction":[77],"oxyanion":[80],"hole":[81],"near":[82],"S1":[84],"subsite":[85],"multiple":[87],"hydrogen":[88],"bonds.":[89]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2023,"cited_by_count":2},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":3},{"year":2016,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-07-22T00:00:00"}