{"id":"https://openalex.org/W2073990481","doi":"https://doi.org/10.1021/ja9815071","title":"Intramolecular Catalysis of Amide Isomerization: Kinetic Consequences of the 5-NH- -Na Hydrogen Bond in Prolyl Peptides","display_name":"Intramolecular Catalysis of Amide Isomerization: Kinetic Consequences of the 5-NH- -Na Hydrogen Bond in Prolyl Peptides","publication_year":1998,"publication_date":"1998-10-01","ids":{"openalex":"https://openalex.org/W2073990481","doi":"https://doi.org/10.1021/ja9815071","mag":"2073990481"},"language":"en","primary_location":{"id":"doi:10.1021/ja9815071","doi":"https://doi.org/10.1021/ja9815071","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja9815071","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","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/A5067918981","display_name":"Christopher D. Cox","orcid":"https://orcid.org/0000-0001-9986-1561","observed_orcids":["https://orcid.org/0000-0001-9986-1561"]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Christopher Cox","raw_affiliation_strings":["Contribution from the Department of Chemistry, Johns Hopkins University, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, Johns Hopkins University, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5046784729","display_name":"Thomas Lectka","orcid":"https://orcid.org/0000-0003-3088-6714","observed_orcids":["https://orcid.org/0000-0003-3088-6714"]},"institutions":[{"id":"https://openalex.org/I145311948","display_name":"Johns Hopkins University","ror":"https://ror.org/00za53h95","country_code":"US","type":"education","lineage":["https://openalex.org/I145311948"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Thomas Lectka","raw_affiliation_strings":["Contribution from the Department of Chemistry, Johns Hopkins University, Baltimore, Maryland, 21218"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, Johns Hopkins University, Baltimore, Maryland, 21218","institution_ids":["https://openalex.org/I145311948"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I145311948"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.5329,"has_fulltext":false,"cited_by_count":86,"citation_normalized_percentile":{"value":0.82437207,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"120","issue":"41","first_page":"10660","last_page":"10668"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10044","display_name":"Protein Structure and Dynamics","score":0.2883000075817108,"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"}},"topics":[{"id":"https://openalex.org/T10044","display_name":"Protein Structure and Dynamics","score":0.2883000075817108,"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/T12620","display_name":"Signaling Pathways in Disease","score":0.26980000734329224,"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":0.17270000278949738,"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/peptidylprolyl-isomerase","display_name":"peptidylprolyl isomerase","score":0.9459999799728394},{"id":"https://openalex.org/keywords/proline-cis-trans-isomerization","display_name":"proline cis-trans isomerization","score":0.8579999804496765},{"id":"https://openalex.org/keywords/intramolecular-hydrogen-bonding","display_name":"intramolecular hydrogen bonding","score":0.9549999833106995},{"id":"https://openalex.org/keywords/general-acid-catalysis","display_name":"general acid catalysis","score":0.8140000104904175},{"id":"https://openalex.org/keywords/reaction-kinetics","display_name":"reaction kinetics","score":0.6890000104904175},{"id":"https://openalex.org/keywords/five-membered-rings","display_name":"five-membered rings","score":0.753000020980835}],"concepts":[{"id":"https://openalex.org/C126661725","wikidata":"https://www.wikidata.org/wiki/Q903420","display_name":"Isomerization","level":3,"score":0.95637047290802},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9487071633338928},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.8772273063659668},{"id":"https://openalex.org/C2778439535","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Amide","level":2,"score":0.7235943078994751},{"id":"https://openalex.org/C2781264208","wikidata":"https://www.wikidata.org/wiki/Q118026","display_name":"Isomerase","level":3,"score":0.6281087398529053},{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.5773906707763672},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.5739225745201111},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5650367140769958},{"id":"https://openalex.org/C31684184","wikidata":"https://www.wikidata.org/wiki/Q33293","display_name":"Peptide bond","level":3,"score":0.5504150390625},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.3305986523628235},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.21566742658615112},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.18720176815986633},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.1511416733264923}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/ja9815071","doi":"https://doi.org/10.1021/ja9815071","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja9815071","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":46,"referenced_works":["https://openalex.org/W262890394","https://openalex.org/W323363336","https://openalex.org/W625272620","https://openalex.org/W641157248","https://openalex.org/W1039083189","https://openalex.org/W1569706722","https://openalex.org/W1588317987","https://openalex.org/W1969971113","https://openalex.org/W1970245419","https://openalex.org/W1973733815","https://openalex.org/W1974790505","https://openalex.org/W1978852647","https://openalex.org/W1990155176","https://openalex.org/W2017639307","https://openalex.org/W2018912911","https://openalex.org/W2021651548","https://openalex.org/W2023579978","https://openalex.org/W2029325972","https://openalex.org/W2029925216","https://openalex.org/W2030497718","https://openalex.org/W2030841140","https://openalex.org/W2035177298","https://openalex.org/W2039490370","https://openalex.org/W2039519959","https://openalex.org/W2041349943","https://openalex.org/W2052242529","https://openalex.org/W2057709509","https://openalex.org/W2064443313","https://openalex.org/W2064542810","https://openalex.org/W2070830434","https://openalex.org/W2071911426","https://openalex.org/W2078141863","https://openalex.org/W2078297860","https://openalex.org/W2082254926","https://openalex.org/W2090471175","https://openalex.org/W2092722500","https://openalex.org/W2110488097","https://openalex.org/W2114858319","https://openalex.org/W2164693316","https://openalex.org/W2949181921","https://openalex.org/W2949803888","https://openalex.org/W2949860131","https://openalex.org/W2951362554","https://openalex.org/W2951483079","https://openalex.org/W3004623155","https://openalex.org/W4233624775"],"related_works":["https://openalex.org/W2061112696","https://openalex.org/W1975854921","https://openalex.org/W2037344831","https://openalex.org/W2035816454","https://openalex.org/W2080964159","https://openalex.org/W1992026608","https://openalex.org/W2041349943","https://openalex.org/W1995859864","https://openalex.org/W117391014","https://openalex.org/W1966041651"],"abstract_inverted_index":{"The":[0],"presence":[1],"of":[2,18,40,58,86,105],"an":[3,59],"intramolecular":[4,60,106],"hydrogen":[5,61,81],"bond":[6,62],"has":[7],"been":[8],"proposed":[9],"to":[10,92],"play":[11],"a":[12,74,80],"key":[13],"role":[14],"in":[15,43,94],"the":[16,35,56,64,69,101],"catalysis":[17],"amide":[19,66,108],"isomerization":[20,39,89],"by":[21,90],"peptidylprolyl":[22],"isomerases":[23],"(PPIases),":[24],"which":[25],"are":[26],"highly":[27],"conserved":[28],"and":[29,45,51,68],"ubiquitous":[30],"rotamase":[31],"enzymes":[32],"that":[33,54,83],"catalyze":[34],"cis":[36],"\u2212":[37],"trans":[38],"proline":[41,88],"residues":[42],"peptides":[44],"proteins.":[46],"We":[47],"present":[48],"herein":[49],"kinetic":[50],"spectroscopic":[52],"evidence":[53],"indicates":[55],"existence":[57],"between":[63],"prolyl":[65,96],"nitrogen":[67],"adjacent":[70],"amidic":[71],"NH":[72],"within":[73],"five-membered":[75],"ring":[76],"(the":[77],"5-NH-":[78],"-N":[79],"bond)":[82],"is":[84],"capable":[85],"catalyzing":[87],"up":[91],"260-fold":[93],"model":[95],"peptides.":[97],"Our":[98],"results":[99],"provide":[100],"first":[102],"systematic":[103],"study":[104],"general-acid-catalyzed":[107],"isomerization.":[109]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2023,"cited_by_count":3},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":3},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":5},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":4},{"year":2012,"cited_by_count":3}],"updated_date":"2026-10-08T09:06:37.294493","created_date":"2016-06-24T00:00:00"}