{"id":"https://openalex.org/W2003138126","doi":"https://doi.org/10.1021/jm00211a025","title":"Synthesis and some pharmacological properties of [4-threonine,7-glycine]oxytocin, [1-(L-2-hydroxy-3-mercaptopropanoic acid),4-threonine,7-glycine]oxytocin (hydroxy[thr4, gly7]oxytocin), and [7-glycine]oxytocin, peptides with high oxytocic-antidiuretic selectivity","display_name":"Synthesis and some pharmacological properties of [4-threonine,7-glycine]oxytocin, [1-(L-2-hydroxy-3-mercaptopropanoic acid),4-threonine,7-glycine]oxytocin (hydroxy[thr4, gly7]oxytocin), and [7-glycine]oxytocin, peptides with high oxytocic-antidiuretic selectivity","publication_year":1977,"publication_date":"1977-01-01","ids":{"openalex":"https://openalex.org/W2003138126","doi":"https://doi.org/10.1021/jm00211a025","mag":"2003138126","pmid":"https://pubmed.ncbi.nlm.nih.gov/833810"},"language":"en","primary_location":{"id":"doi:10.1021/jm00211a025","doi":"https://doi.org/10.1021/jm00211a025","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00211a025","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","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 Medicinal 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/A5070921069","display_name":"John Lowbridge","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"John Lowbridge","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110409708","display_name":"Maurice Manning","orcid":"https://orcid.org/0000-0002-0051-5149","observed_orcids":["https://orcid.org/0000-0002-0051-5149"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Maurice Manning","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5004687937","display_name":"Jaya Haldar","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Jaya Haldar","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5109103296","display_name":"Wilbur H. Sawyer","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Wilbur H. Sawyer","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.5547,"has_fulltext":false,"cited_by_count":98,"citation_normalized_percentile":{"value":0.59272275,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"20","issue":"1","first_page":"120","last_page":"123"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.9682999849319458,"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":0.9682999849319458,"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/T11541","display_name":"Neuroendocrine regulation and behavior","score":0.024700000882148743,"subfield":{"id":"https://openalex.org/subfields/3207","display_name":"Social Psychology"},"field":{"id":"https://openalex.org/fields/32","display_name":"Psychology"},"domain":{"id":"https://openalex.org/domains/2","display_name":"Social Sciences"}},{"id":"https://openalex.org/T10814","display_name":"Neuropeptides and Animal Physiology","score":0.003599999938160181,"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/oxytocin-analogs","display_name":"oxytocin analogues","score":0.9539999961853027},{"id":"https://openalex.org/keywords/oxytocic-activity","display_name":"oxytocic activity","score":0.8550000190734863},{"id":"https://openalex.org/keywords/antidiuretic-activity","display_name":"antidiuretic activity","score":0.996999979019165},{"id":"https://openalex.org/keywords/threonine-substitution","display_name":"threonine substitution","score":0.9300000071525574},{"id":"https://openalex.org/keywords/magnesium-sensitivity","display_name":"magnesium sensitivity","score":0.7279999852180481},{"id":"https://openalex.org/keywords/uterine-contraction","display_name":"uterine contraction","score":0.5339999794960022},{"id":"https://openalex.org/keywords/peptide-synthesis","display_name":"peptide synthesis","score":0.5210000276565552},{"id":"https://openalex.org/keywords/solid-phase-peptide-synthesis","display_name":"solid-phase peptide synthesis","score":0.6520000100135803}],"concepts":[{"id":"https://openalex.org/C2776176026","wikidata":"https://www.wikidata.org/wiki/Q169960","display_name":"Oxytocin","level":2,"score":0.9680781364440918},{"id":"https://openalex.org/C2777756961","wikidata":"https://www.wikidata.org/wiki/Q620730","display_name":"Glycine","level":3,"score":0.8978865146636963},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8794553279876709},{"id":"https://openalex.org/C2775880066","wikidata":"https://www.wikidata.org/wiki/Q186521","display_name":"Threonine","level":4,"score":0.723708987236023},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.3779502213001251},{"id":"https://openalex.org/C2776414213","wikidata":"https://www.wikidata.org/wiki/Q183290","display_name":"Serine","level":3,"score":0.37313294410705566},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.36770057678222656},{"id":"https://openalex.org/C134018914","wikidata":"https://www.wikidata.org/wiki/Q162606","display_name":"Endocrinology","level":1,"score":0.21670442819595337},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.06693911552429199},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.05669510364532471}],"mesh":[{"descriptor_ui":"D000603","descriptor_name":"Amino Acids, Sulfur","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D005998","descriptor_name":"Glycine","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006900","descriptor_name":"Hydroxylation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008625","descriptor_name":"Tiopronin","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D008722","descriptor_name":"Methods","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009842","descriptor_name":"Oligopeptides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D010121","descriptor_name":"Oxytocin","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D010121","descriptor_name":"Oxytocin","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D013912","descriptor_name":"Threonine","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D014667","descriptor_name":"Vasopressins","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jm00211a025","doi":"https://doi.org/10.1021/jm00211a025","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00211a025","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","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 Medicinal Chemistry","raw_type":"journal-article"},{"id":"pmid:833810","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/833810","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":"Journal of medicinal chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Good health and well-being","score":0.5683000087738037,"id":"https://metadata.un.org/sdg/3"}],"sustainable_development_goals_aurora":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W2039536421","https://openalex.org/W2328170314","https://openalex.org/W2069086700","https://openalex.org/W2320320028","https://openalex.org/W2042757781","https://openalex.org/W1991691117","https://openalex.org/W2475288103","https://openalex.org/W1985186583","https://openalex.org/W1999534434","https://openalex.org/W2095199356"],"abstract_inverted_index":{"[4-Threonine,":[0,103],"7-glycine]oxytocin":[1,6,104],"and":[2,16,31,34,50,85,114,141,160,191],"[1-(L-2-hydroxy-3-mercaptopropanoic":[3],"acid),":[4],"4-threonine,":[5],"(hydroxy[Thr4,":[7],"Gly7]oxytocin)":[8],"were":[9,42],"synthesized":[10,26],"by":[11,27],"a":[12,59,135,142,180,220],"combination":[13],"of":[14,19,61,71,80,90,100,109,118,155,163,195,205,223],"solid-phase":[15,29],"classical":[17],"methods":[18],"peptide":[20],"synthesis.":[21],"A":[22],"protected":[23,63],"octapeptide":[24,52],"was":[25,56],"the":[28,46,62,68,186,193,203,233],"method":[30],"following":[32],"ammonolysis":[33],"purification":[35],"1":[36],"+":[37],"8":[38,158],"couplings":[39],"in":[40,67,138,145,192,202,215,227,231],"solution":[41],"employed":[43],"to":[44,183],"furnish":[45],"required":[47],"key":[48],"nonapeptide":[49,64],"acyl":[51],"intermediates,":[53],"respectively.":[54],"[7-Glycine]oxytocin":[55,74],"prepared":[57],"from":[58],"sample":[60],"intermediate":[65],"used":[66],"original":[69],"synthesis":[70],"this":[72],"peptide.":[73],"has":[75,96,105,131,151],"an":[76,86,97,106,115,152],"oxytocic":[77,107,139,153,200,213],"potency":[78,88,108,117,154,162],"(O)":[79],"93":[81],"+/-":[82,92,111,120,157,165],"4":[83,112],"units/mg":[84,113,159],"antidiuretic":[87,116,161],"(A)":[89],"0.0056":[91],"0.0003":[93],"units/mg.":[94,122,167,207],"It":[95],"O/A":[98,124,146,169],"ratio":[99,125,170],"16":[101],"000.":[102,128],"166":[110],"0.002":[119],"0.0004":[121],"Its":[123,168],"is":[126,171,235],"83":[127],"Threonine":[129],"substitution":[130],"thus":[132,172],"brought":[133],"about":[134],"substantial":[136],"enhancement":[137,144],"activity":[140],"fivefold":[143],"selectivity.":[147],"Hydroxy":[148],"[Thr4,":[149],"Gly7]oxytocin":[150],"218":[156],"0.0040":[164],"0.0005":[166],"54":[173],"500.":[174],"All":[175],"three":[176],"7-glycine-substituted":[177],"analogues":[178],"exhibit":[179,211],"marked":[181],"sensitivity":[182],"Mg2+":[184,198],"on":[185],"rat":[187],"uterus":[188],"assay":[189],"ststem":[190],"presence":[194],"0.5":[196],"mM":[197],"had":[199],"potencies":[201],"range":[204],"900-1000":[206],"Should":[208],"these":[209],"peptides":[210],"enhanced":[212],"selectivity":[214],"humans,":[216],"they":[217],"might":[218],"offer":[219],"greater":[221],"margin":[222],"safety":[224],"than":[225],"oxytocin":[226],"those":[228],"clinical":[229],"stiuations":[230],"which":[232],"latter":[234],"currently":[236],"employed.":[237]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2021,"cited_by_count":2},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":3},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":5},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}