{"id":"https://openalex.org/W1977413889","doi":"https://doi.org/10.1039/a708832i","title":"Investigation of the applicability of cis-urocanic acid as a model for the catalytic Asp\u2013His dyad in the active site of serine proteases based on 1H NMR hydrogen bonding studies and spectroscopic pKa measurements","display_name":"Investigation of the applicability of cis-urocanic acid as a model for the catalytic Asp\u2013His dyad in the active site of serine proteases based on 1H NMR hydrogen bonding studies and spectroscopic pKa measurements","publication_year":1998,"publication_date":"1998-01-01","ids":{"openalex":"https://openalex.org/W1977413889","doi":"https://doi.org/10.1039/a708832i","mag":"1977413889"},"language":"en","primary_location":{"id":"doi:10.1039/a708832i","doi":"https://doi.org/10.1039/a708832i","is_oa":false,"landing_page_url":"https://doi.org/10.1039/a708832i","pdf_url":null,"source":{"id":"https://openalex.org/S4210187049","display_name":"Journal of the Chemical Society Perkin Transactions 2","issn_l":"0300-9580","issn":["0300-9580","1364-5471","1472-779X","2050-8239"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"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":"Journal of the Chemical Society, Perkin Transactions 2","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/A5075823048","display_name":"Helmi Neuvonen","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Helmi Neuvonen","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5020694408","display_name":"Kari Neuvonen","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Kari Neuvonen","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":0.3033,"has_fulltext":false,"cited_by_count":7,"citation_normalized_percentile":{"value":0.50533834,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":95},"biblio":{"volume":null,"issue":"7","first_page":"1665","last_page":"1670"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12191","display_name":"Chemical Reaction Mechanisms","score":0.961899995803833,"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/T12191","display_name":"Chemical Reaction Mechanisms","score":0.961899995803833,"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/T10620","display_name":"Protease and Inhibitor Mechanisms","score":0.007600000128149986,"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/T12410","display_name":"Structural and Chemical Analysis of Organic and Inorganic Compounds","score":0.005499999970197678,"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/cis-urocanic-acid","display_name":"cis-urocanic acid","score":1.0},{"id":"https://openalex.org/keywords/serine-protease-active-site","display_name":"serine protease active site","score":0.972000002861023},{"id":"https://openalex.org/keywords/intramolecular-hydrogen-bonding","display_name":"intramolecular hydrogen bonding","score":0.871999979019165},{"id":"https://openalex.org/keywords/imidazole-derivatives","display_name":"imidazole derivatives","score":0.8759999871253967},{"id":"https://openalex.org/keywords/1h-chemical-shifts","display_name":"1H NMR chemical shifts","score":0.796999990940094},{"id":"https://openalex.org/keywords/pka-determination","display_name":"pKa determination","score":0.6579999923706055},{"id":"https://openalex.org/keywords/nucleophilicity","display_name":"nucleophilicity","score":0.7730000019073486},{"id":"https://openalex.org/keywords/complex-formation","display_name":"complex formation","score":0.7549999952316284},{"id":"https://openalex.org/keywords/dimethyl-sulfoxide","display_name":"dimethyl sulfoxide","score":0.6190000176429749}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8962650299072266},{"id":"https://openalex.org/C2780874372","wikidata":"https://www.wikidata.org/wiki/Q328692","display_name":"Imidazole","level":2,"score":0.8467122912406921},{"id":"https://openalex.org/C2776381347","wikidata":"https://www.wikidata.org/wiki/Q30536","display_name":"Urocanic acid","level":4,"score":0.8104900121688843},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.7457975745201111},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.6525249481201172},{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.6043610572814941},{"id":"https://openalex.org/C2776414213","wikidata":"https://www.wikidata.org/wiki/Q183290","display_name":"Serine","level":3,"score":0.4688224494457245},{"id":"https://openalex.org/C2778460671","wikidata":"https://www.wikidata.org/wiki/Q485277","display_name":"Histidine","level":3,"score":0.4618382155895233},{"id":"https://openalex.org/C103319777","wikidata":"https://www.wikidata.org/wiki/Q1979695","display_name":"Proton NMR","level":2,"score":0.44923311471939087},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.43695518374443054},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.4104146957397461},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.40942347049713135},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.252840518951416},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.17136645317077637},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.11732953786849976}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1039/a708832i","doi":"https://doi.org/10.1039/a708832i","is_oa":false,"landing_page_url":"https://doi.org/10.1039/a708832i","pdf_url":null,"source":{"id":"https://openalex.org/S4210187049","display_name":"Journal of the Chemical Society Perkin Transactions 2","issn_l":"0300-9580","issn":["0300-9580","1364-5471","1472-779X","2050-8239"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"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":"Journal of the Chemical Society, Perkin Transactions 2","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":47,"referenced_works":["https://openalex.org/W1490997128","https://openalex.org/W1491027295","https://openalex.org/W1581340549","https://openalex.org/W1966964730","https://openalex.org/W1970543775","https://openalex.org/W1971013674","https://openalex.org/W1972909438","https://openalex.org/W1980494973","https://openalex.org/W1989338402","https://openalex.org/W1990618646","https://openalex.org/W1995948694","https://openalex.org/W1997537943","https://openalex.org/W1998312296","https://openalex.org/W2000374093","https://openalex.org/W2001660361","https://openalex.org/W2002051063","https://openalex.org/W2003727400","https://openalex.org/W2005293507","https://openalex.org/W2014688483","https://openalex.org/W2017766716","https://openalex.org/W2021123286","https://openalex.org/W2029381760","https://openalex.org/W2041556739","https://openalex.org/W2054638130","https://openalex.org/W2067887310","https://openalex.org/W2076036516","https://openalex.org/W2078666498","https://openalex.org/W2084894904","https://openalex.org/W2088459176","https://openalex.org/W2155604981","https://openalex.org/W2217122178","https://openalex.org/W2237038000","https://openalex.org/W2263298170","https://openalex.org/W2320470116","https://openalex.org/W2326630050","https://openalex.org/W2326856942","https://openalex.org/W2401288026","https://openalex.org/W2437153424","https://openalex.org/W2949856865","https://openalex.org/W2950237331","https://openalex.org/W2950990513","https://openalex.org/W2952035731","https://openalex.org/W2952067095","https://openalex.org/W2952684232","https://openalex.org/W2952783678","https://openalex.org/W3004842070","https://openalex.org/W3005489507"],"related_works":["https://openalex.org/W2072580555","https://openalex.org/W2075324957","https://openalex.org/W1971013674","https://openalex.org/W2375541495","https://openalex.org/W2059695883","https://openalex.org/W2015773654","https://openalex.org/W1542113835","https://openalex.org/W2060042542","https://openalex.org/W1523437238","https://openalex.org/W1966964730"],"abstract_inverted_index":{"The":[0,77,107],"intramolecular":[1,74],"hydrogen":[2,75],"bond":[3],"of":[4,26,39,51,55,80,86,94,104,115,131,143],"cis-urocanic":[5],"acid,":[6],"(Z)-3-(1H-imidazol-4-yl)prop-2-enoic":[7],"acid":[8],"(cis-UCA)":[9],"in":[10,35,134],"DMSO":[11,135],"has":[12,89,145],"been":[13,90,138,146],"evaluated":[14],"by":[15],"the":[16,24,32,36,43,48,52,83,95,102,113,123],"1H":[17],"NMR":[18],"chemical":[19],"shift":[20],"approach":[21],"to":[22,119],"assess":[23],"suitability":[25],"cis-UCA":[27,56,81,116],"as":[28],"a":[29,70,141],"model":[30],"for":[31,112,148],"Asp\u2013His":[33],"dyad":[34],"active":[37],"site":[38],"serine":[40],"proteases.":[41],"Both":[42],"acidic":[44],"OH":[45],"proton":[46,50],"and":[47,65,97,127,140],"C2":[49],"imidazole":[53,99,132],"ring":[54],"resonate":[57],"at":[58,62],"exceptionally":[59],"low":[60],"field,":[61],"ca.":[63],"17.4":[64],"8.2":[66],"ppm,":[67],"respectively,":[68],"indicating":[69],"strong":[71],"N\u2013H\u2013O":[72],"type":[73],"bond.":[76],"nucleophilic":[78],"reactivity":[79],"toward":[82],"acyl":[84,125],"carbon":[85],"4-nitrophenyl":[87],"chloroacetate":[88],"compared":[91],"with":[92,101,122],"that":[93],"trans-isomer":[96],"other":[98],"derivatives":[100,133],"aid":[103],"kinetic":[105,109],"studies.":[106],"non-linear":[108],"behaviour":[110],"observed":[111,147],"reaction":[114],"is":[117],"attributed":[118],"complex":[120],"formation":[121],"reacting":[124],"derivative":[126],"cis-UCA.":[128,149],"pKa":[129],"determinations":[130],"have":[136],"also":[137],"performed":[139],"value":[142],"3.2":[144]},"counts_by_year":[{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2013,"cited_by_count":1}],"updated_date":"2026-07-28T07:46:37.118299","created_date":"2016-06-24T00:00:00"}
