{"id":"https://openalex.org/W1973062644","doi":"https://doi.org/10.1021/jo991288h","title":"Cyclopropane-Derived Peptidomimetics. Design, Synthesis, and Evaluation of Novel Enkephalin Analogues","display_name":"Cyclopropane-Derived Peptidomimetics. Design, Synthesis, and Evaluation of Novel Enkephalin Analogues","publication_year":2000,"publication_date":"2000-02-09","ids":{"openalex":"https://openalex.org/W1973062644","doi":"https://doi.org/10.1021/jo991288h","mag":"1973062644","pmid":"https://pubmed.ncbi.nlm.nih.gov/10814090"},"language":"en","primary_location":{"id":"doi:10.1021/jo991288h","doi":"https://doi.org/10.1021/jo991288h","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo991288h","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic 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/A5055989647","display_name":"Stephen F. Martin","orcid":"https://orcid.org/0000-0002-4639-0695","observed_orcids":["https://orcid.org/0000-0002-4639-0695"]},"institutions":[{"id":"https://openalex.org/I86519309","display_name":"The University of Texas at Austin","ror":"https://ror.org/00hj54h04","country_code":"US","type":"education","lineage":["https://openalex.org/I86519309"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Stephen F. Martin","raw_affiliation_strings":["Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712","Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712 USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712","institution_ids":["https://openalex.org/I86519309"]},{"raw_affiliation_string":"Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712 USA","institution_ids":["https://openalex.org/I86519309"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5111859699","display_name":"Michael P. Dwyer","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I86519309","display_name":"The University of Texas at Austin","ror":"https://ror.org/00hj54h04","country_code":"US","type":"education","lineage":["https://openalex.org/I86519309"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Michael P. Dwyer","raw_affiliation_strings":["Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712","institution_ids":["https://openalex.org/I86519309"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5077919150","display_name":"Beno\u0131\u0302t Hartmann","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I86519309","display_name":"The University of Texas at Austin","ror":"https://ror.org/00hj54h04","country_code":"US","type":"education","lineage":["https://openalex.org/I86519309"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Beno\u00eet Hartmann","raw_affiliation_strings":["Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712","institution_ids":["https://openalex.org/I86519309"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5019633714","display_name":"Kyle S. Knight","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I86519309","display_name":"The University of Texas at Austin","ror":"https://ror.org/00hj54h04","country_code":"US","type":"education","lineage":["https://openalex.org/I86519309"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Kyle S. Knight","raw_affiliation_strings":["Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712","institution_ids":["https://openalex.org/I86519309"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I86519309"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.6997,"has_fulltext":false,"cited_by_count":64,"citation_normalized_percentile":{"value":0.83046234,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"65","issue":"5","first_page":"1305","last_page":"1318"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.6333000063896179,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.6333000063896179,"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/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.2937000095844269,"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/T10814","display_name":"Neuropeptides and Animal Physiology","score":0.03519999980926514,"subfield":{"id":"https://openalex.org/subfields/2804","display_name":"Cellular and Molecular Neuroscience"},"field":{"id":"https://openalex.org/fields/28","display_name":"Neuroscience"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/peptidomimetics","display_name":"peptidomimetics","score":0.8960000276565552},{"id":"https://openalex.org/keywords/enkephalin-analogs","display_name":"enkephalin analogs","score":0.9300000071525574},{"id":"https://openalex.org/keywords/leu-enkephalin","display_name":"leu-enkephalin","score":0.984000027179718},{"id":"https://openalex.org/keywords/opioid-receptor-binding","display_name":"opioid receptor binding","score":0.6349999904632568},{"id":"https://openalex.org/keywords/mu-opioid-receptor","display_name":"mu-opioid receptor","score":0.8889999985694885},{"id":"https://openalex.org/keywords/enantioselective-cyclization","display_name":"enantioselective cyclization","score":0.8100000023841858},{"id":"https://openalex.org/keywords/peptide-conformation","display_name":"peptide conformation","score":0.5440000295639038}],"concepts":[{"id":"https://openalex.org/C124790011","wikidata":"https://www.wikidata.org/wiki/Q2069797","display_name":"Peptidomimetic","level":3,"score":0.9490733742713928},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9490350484848022},{"id":"https://openalex.org/C2779200411","wikidata":"https://www.wikidata.org/wiki/Q80250","display_name":"Cyclopropane","level":3,"score":0.9380122423171997},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5354167819023132},{"id":"https://openalex.org/C2777803847","wikidata":"https://www.wikidata.org/wiki/Q325101","display_name":"Enkephalin","level":4,"score":0.5265165567398071},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4405498802661896},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2491668462753296},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.22041243314743042},{"id":"https://openalex.org/C2781063702","wikidata":"https://www.wikidata.org/wiki/Q427523","display_name":"Opioid","level":3,"score":0.16594433784484863},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.12405967712402344},{"id":"https://openalex.org/C2779281246","wikidata":"https://www.wikidata.org/wiki/Q172847","display_name":"Peptide","level":2,"score":0.08863264322280884},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.05180191993713379}],"mesh":[{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001667","descriptor_name":"Binding, Competitive","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001921","descriptor_name":"Brain","qualifier_ui":"Q000166","qualifier_name":"cytology","is_major_topic":false},{"descriptor_ui":"D001921","descriptor_name":"Brain","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D002462","descriptor_name":"Cell Membrane","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D003500","descriptor_name":"Cyclization","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003521","descriptor_name":"Cyclopropanes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D003521","descriptor_name":"Cyclopropanes","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D003521","descriptor_name":"Cyclopropanes","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D003521","descriptor_name":"Cyclopropanes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D004743","descriptor_name":"Enkephalin, Leucine","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D004743","descriptor_name":"Enkephalin, Leucine","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004743","descriptor_name":"Enkephalin, Leucine","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D004743","descriptor_name":"Enkephalin, Leucine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006168","descriptor_name":"Guinea Pigs","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007082","descriptor_name":"Ileum","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D008297","descriptor_name":"Male","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011485","descriptor_name":"Protein Binding","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011957","descriptor_name":"Receptors, Opioid","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D014649","descriptor_name":"Vas Deferens","qualifier_ui":"Q000187","qualifier_name":"drug effects","is_major_topic":false},{"descriptor_ui":"D015195","descriptor_name":"Drug Design","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D018716","descriptor_name":"Molecular Mimicry","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D020128","descriptor_name":"Inhibitory Concentration 50","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D051379","descriptor_name":"Mice","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo991288h","doi":"https://doi.org/10.1021/jo991288h","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo991288h","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:10814090","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/10814090","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 organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320337347","display_name":"National Institute on Drug Abuse","ror":"https://ror.org/00fq5cm18"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":26,"referenced_works":["https://openalex.org/W1483120923","https://openalex.org/W1522993790","https://openalex.org/W1977341219","https://openalex.org/W1982696949","https://openalex.org/W1984710000","https://openalex.org/W1999210337","https://openalex.org/W2009853074","https://openalex.org/W2011082893","https://openalex.org/W2021928628","https://openalex.org/W2027213561","https://openalex.org/W2032613914","https://openalex.org/W2032761582","https://openalex.org/W2037771701","https://openalex.org/W2050613574","https://openalex.org/W2057891684","https://openalex.org/W2076635161","https://openalex.org/W2077993028","https://openalex.org/W2085891026","https://openalex.org/W2088083959","https://openalex.org/W2092799614","https://openalex.org/W2126533930","https://openalex.org/W2432110457","https://openalex.org/W2950031194","https://openalex.org/W2952780718","https://openalex.org/W4238091855","https://openalex.org/W4290430159"],"related_works":["https://openalex.org/W1976363899","https://openalex.org/W1989638387","https://openalex.org/W2174574070","https://openalex.org/W1993111639","https://openalex.org/W2066984259","https://openalex.org/W2116799924","https://openalex.org/W2031887579","https://openalex.org/W159761704","https://openalex.org/W2025707537","https://openalex.org/W2050613574"],"abstract_inverted_index":{"It":[0],"is":[1,57],"known":[2],"that":[3,20,87],"peptide":[4],"mimics":[5],"containing":[6,67,153,167],"trans-substituted":[7],"cyclopropanes":[8,41],"stabilize":[9,27],"extended":[10],"conformations":[11],"of":[12,39,46,75,92,107,117,130,144,156,182],"oligopeptides,":[13],"and":[14,49,81,102,123,146,149],"molecular":[15],"modeling":[16],"studies":[17],"now":[18],"suggest":[19],"the":[21,47,73,76,89,97,108,115,118,128,157,164,171,183],"corresponding":[22],"cis-cyclopropane":[23],"dipeptide":[24,51,78],"isosteres":[25,79],"could":[26],"a":[28,37,65,68,85,124,142],"reverse":[29],"turn.":[30],"To":[31],"begin":[32],"to":[33,59,61,114,180],"assess":[34],"this":[35],"possibility,":[36],"series":[38],"cis-substituted":[40],"were":[42,139],"incorporated":[43],"as":[44],"replacements":[45,155,169],"Gly(2)-Gly(3)":[48,158],"Phe(4)-Leu(5)":[50,172],"subunits":[52],"in":[53,64,141],"Leu-enkephalin":[54,137],"(H(2)N-Tyr-Gly-Gly-Phe-Leu-OH),":[55],"which":[56],"believed":[58],"bind":[60,176],"opiod":[62],"receptors":[63],"conformation":[66],"beta-turn.":[69],"General":[70],"methods":[71],"for":[72,127,163,170],"synthesis":[74,129],"cyclopropane-containing":[77],"-XaaPsi[COcpCO]Yaa-":[80],"-XaaPsi[NHcpNH]Yaa-were":[82],"developed":[83],"by":[84,96],"sequence":[86],"featured":[88],"enantioselective":[90],"cyclization":[91],"allylic":[93],"diazoacetates":[94],"catalyzed":[95],"chiral":[98],"rhodium":[99],"complexes":[100],"Rh(2)[(5S)-MEPY](4)":[101],"Rh(2)[(5R)-MEPY](4).":[103],"A":[104],"useful":[105],"modification":[106],"Weinreb":[109],"amidation":[110],"procedure":[111],"was":[112,133],"applied":[113],"opening":[116],"intermediate":[119],"lactones":[120],"with":[121,177],"dipeptides,":[122],"novel":[125],"method":[126],"substituted":[131],"diaminocyclopropanes":[132],"also":[134],"developed.":[135],"The":[136],"analogues":[138,166],"tested":[140],"panel":[143],"binding":[145],"functional":[147],"assays,":[148],"although":[150],"those":[151],"derivatives":[152],"cyclopropane":[154],"exhibited":[159],"low":[160],"micromolar":[161],"affinity":[162,179],"mu-receptor,":[165],"such":[168],"subunit":[173],"did":[174],"not":[175],"significant":[178],"any":[181],"opioid":[184],"receptors.":[185],"These":[186],"results":[187],"are":[188],"discussed.":[189]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":2},{"year":2022,"cited_by_count":4},{"year":2021,"cited_by_count":2},{"year":2017,"cited_by_count":3},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":2},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":5},{"year":2012,"cited_by_count":4}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}