{"id":"https://openalex.org/W2047762856","doi":"https://doi.org/10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","title":"Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates","display_name":"Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates","publication_year":2000,"publication_date":"2000-01-01","ids":{"openalex":"https://openalex.org/W2047762856","doi":"https://doi.org/10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","mag":"2047762856","pmid":"https://pubmed.ncbi.nlm.nih.gov/10861954"},"language":"en","primary_location":{"id":"doi:10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","doi":"https://doi.org/10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","is_oa":false,"landing_page_url":"https://doi.org/10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","pdf_url":null,"source":{"id":"https://openalex.org/S67976470","display_name":"Chirality","issn_l":"0899-0042","issn":["0899-0042","1520-636X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","medline","norway-1","poland-70","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chirality","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/A5111080596","display_name":"Isaac O. Donkor","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I160606119","display_name":"University of Tennessee Health Science Center","ror":"https://ror.org/0011qv509","country_code":"US","type":"education","lineage":["https://openalex.org/I160606119"]},{"id":"https://openalex.org/I2799495847","display_name":"University of Tennessee System","ror":"https://ror.org/00xzqjh13","country_code":"US","type":"education","lineage":["https://openalex.org/I2799495847"]},{"id":"https://openalex.org/I75027704","display_name":"University of Tennessee at Knoxville","ror":"https://ror.org/020f3ap87","country_code":"US","type":"education","lineage":["https://openalex.org/I75027704"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Isaac O. Donkor","raw_affiliation_strings":["Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee","The University of Tennessee, Faculty Bldg. Room 327, 847 Monroe Avenue, Memphis, TN 38163"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee","institution_ids":["https://openalex.org/I160606119"]},{"raw_affiliation_string":"The University of Tennessee, Faculty Bldg. Room 327, 847 Monroe Avenue, Memphis, TN 38163","institution_ids":["https://openalex.org/I2799495847","https://openalex.org/I75027704"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5112448965","display_name":"Xiaozhang Zheng","orcid":"https://orcid.org/0000-0002-8403-7374","observed_orcids":["https://orcid.org/0000-0002-8403-7374"]},"institutions":[{"id":"https://openalex.org/I160606119","display_name":"University of Tennessee Health Science Center","ror":"https://ror.org/0011qv509","country_code":"US","type":"education","lineage":["https://openalex.org/I160606119"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Xiaozhang Zheng","raw_affiliation_strings":["Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee","institution_ids":["https://openalex.org/I160606119"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100652091","display_name":"Jie Han","orcid":"https://orcid.org/0000-0002-5682-9753","observed_orcids":["https://orcid.org/0000-0002-5682-9753"]},"institutions":[{"id":"https://openalex.org/I160606119","display_name":"University of Tennessee Health Science Center","ror":"https://ror.org/0011qv509","country_code":"US","type":"education","lineage":["https://openalex.org/I160606119"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jie Han","raw_affiliation_strings":["Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee","institution_ids":["https://openalex.org/I160606119"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5077433493","display_name":"Duane D. Miller","orcid":"https://orcid.org/0000-0002-2638-866X","observed_orcids":["https://orcid.org/0000-0002-2638-866X"]},"institutions":[{"id":"https://openalex.org/I160606119","display_name":"University of Tennessee Health Science Center","ror":"https://ror.org/0011qv509","country_code":"US","type":"education","lineage":["https://openalex.org/I160606119"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Duane D. Miller","raw_affiliation_strings":["Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, Tennessee","institution_ids":["https://openalex.org/I160606119"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5111080596"],"corresponding_institution_ids":["https://openalex.org/I160606119","https://openalex.org/I2799495847","https://openalex.org/I75027704"],"apc_list":{"value":4030,"currency":"USD","value_usd":4030},"apc_paid":null,"fwci":1.1142,"has_fulltext":false,"cited_by_count":10,"citation_normalized_percentile":{"value":0.71938654,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":94},"biblio":{"volume":"12","issue":"7","first_page":"551","last_page":"557"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.9628999829292297,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.9628999829292297,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.03189999982714653,"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/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.0013000000035390258,"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/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.9760000109672546},{"id":"https://openalex.org/keywords/stereoisomers","display_name":"stereoisomers","score":0.8989999890327454},{"id":"https://openalex.org/keywords/diastereomers","display_name":"diastereomers","score":0.8360000252723694},{"id":"https://openalex.org/keywords/common-intermediate","display_name":"common intermediate","score":0.6539999842643738},{"id":"https://openalex.org/keywords/peptidomimetic-inhibitors","display_name":"peptidomimetic inhibitors","score":0.8840000033378601},{"id":"https://openalex.org/keywords/calpain-inhibitors","display_name":"calpain inhibitors","score":0.8930000066757202},{"id":"https://openalex.org/keywords/cis-trans-isomers","display_name":"cis-trans isomers","score":0.6439999938011169},{"id":"https://openalex.org/keywords/peptide-conformation","display_name":"peptide conformation","score":0.6650000214576721}],"concepts":[{"id":"https://openalex.org/C124790011","wikidata":"https://www.wikidata.org/wiki/Q2069797","display_name":"Peptidomimetic","level":3,"score":0.9395589828491211},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9329297542572021},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.8302737474441528},{"id":"https://openalex.org/C124668440","wikidata":"https://www.wikidata.org/wiki/Q2305173","display_name":"Chirality (physics)","level":5,"score":0.7708120346069336},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.7353243827819824},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.4381939470767975},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3750394582748413},{"id":"https://openalex.org/C2779281246","wikidata":"https://www.wikidata.org/wiki/Q172847","display_name":"Peptide","level":2,"score":0.2508198022842407},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.21643498539924622},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.12509584426879883},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.10878115892410278},{"id":"https://openalex.org/C2778564446","wikidata":"https://www.wikidata.org/wiki/Q2305173","display_name":"Chiral symmetry","level":3,"score":0.08448013663291931},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C7602139","wikidata":"https://www.wikidata.org/wiki/Q6718","display_name":"Quark","level":2,"score":0.0},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0},{"id":"https://openalex.org/C20621625","wikidata":"https://www.wikidata.org/wiki/Q6961432","display_name":"Nambu\u2013Jona-Lasinio model","level":4,"score":0.0}],"mesh":[{"descriptor_ui":"D000596","descriptor_name":"Amino Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002855","descriptor_name":"Chromatography, Thin Layer","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007202","descriptor_name":"Indicators and Reagents","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007930","descriptor_name":"Leucine","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D007930","descriptor_name":"Leucine","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D007930","descriptor_name":"Leucine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":4,"locations":[{"id":"doi:10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","doi":"https://doi.org/10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","is_oa":false,"landing_page_url":"https://doi.org/10.1002/1520-636x(2000)12:7%3c551::aid-chir1%3e3.0.co;2-c","pdf_url":null,"source":{"id":"https://openalex.org/S67976470","display_name":"Chirality","issn_l":"0899-0042","issn":["0899-0042","1520-636X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","medline","norway-1","poland-70","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chirality","raw_type":"journal-article"},{"id":"doi:10.1002/1520-636x(2000)12:7<551::aid-chir1>3.0.co;2-c","doi":"https://doi.org/10.1002/1520-636x(2000)12:7<551::aid-chir1>3.0.co;2-c","is_oa":false,"landing_page_url":"https://doi.org/10.1002/1520-636x(2000)12:7<551::aid-chir1>3.0.co;2-c","pdf_url":null,"source":{"id":"https://openalex.org/S67976470","display_name":"Chirality","issn_l":"0899-0042","issn":["0899-0042","1520-636X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","medline","norway-1","poland-70","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chirality","raw_type":"journal-article"},{"id":"doi:10.1002/1520-636x(2000)12:7<551::aid-chir1>3.3.co;2-3","doi":"https://doi.org/10.1002/1520-636x(2000)12:7<551::aid-chir1>3.3.co;2-3","is_oa":false,"landing_page_url":"https://doi.org/10.1002/1520-636x(2000)12:7<551::aid-chir1>3.3.co;2-3","pdf_url":null,"source":{"id":"https://openalex.org/S67976470","display_name":"Chirality","issn_l":"0899-0042","issn":["0899-0042","1520-636X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","medline","norway-1","poland-70","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chirality","raw_type":"journal-article"},{"id":"pmid:10861954","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/10861954","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":"Chirality","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G979984621","display_name":"DEVELOPING SELECTIVE CALPAIN INHIBITORS","funder_award_id":"K14HL003536","funder_id":"https://openalex.org/F4320337338","funder_display_name":"National Heart, Lung, and Blood Institute"}],"funders":[{"id":"https://openalex.org/F4320332505","display_name":"U.S. Public Health Service","ror":"https://ror.org/05xf94514"},{"id":"https://openalex.org/F4320337338","display_name":"National Heart, Lung, and Blood Institute","ror":"https://ror.org/012pb6c26"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":13,"referenced_works":["https://openalex.org/W1522993790","https://openalex.org/W1972864088","https://openalex.org/W1979534840","https://openalex.org/W1994586359","https://openalex.org/W1995987863","https://openalex.org/W2021125774","https://openalex.org/W2021250492","https://openalex.org/W2036845887","https://openalex.org/W2042216234","https://openalex.org/W2063645684","https://openalex.org/W2078069175","https://openalex.org/W2950349801","https://openalex.org/W2951131708"],"related_works":["https://openalex.org/W2034570124","https://openalex.org/W2021125774","https://openalex.org/W2738573600","https://openalex.org/W1985004538","https://openalex.org/W2949171647","https://openalex.org/W2951610554","https://openalex.org/W1971297357","https://openalex.org/W1972560726","https://openalex.org/W2323777844","https://openalex.org/W2950725493"],"abstract_inverted_index":{"2,3-Methanoamino":[0],"acids":[1,47],"are":[2],"useful":[3],"probes":[4],"for":[5,13,35],"studying":[6],"the":[7,15,22,43,60],"bioactive":[8],"conformation":[9],"of":[10,17,24,31,40,45,62,64],"peptides":[11],"and":[12],"investigating":[14],"effect":[16],"local":[18],"conformational":[19],"constraints":[20],"on":[21],"activity":[23],"peptidomimetics.":[25],"We":[26],"synthesized":[27,69],"all":[28],"four":[29],"stereoisomers":[30],"Cbz-protected":[32],"2,":[33],"3-methanoleucine":[34],"incorporation":[36],"into":[37],"peptidomimetic":[38],"inhibitors":[39],"calpain.":[41],"While":[42],"synthesis":[44],"2,3-methanoamino":[46],"has":[48],"been":[49],"previously":[50],"reported,":[51],"our":[52],"procedure":[53],"offers":[54],"a":[55,71],"versatile":[56],"route":[57],"in":[58],"which":[59],"pair":[61],"diastereomers":[63],"each":[65],"geometric":[66],"isomer":[67],"was":[68],"from":[70],"common":[72],"intermediate.":[73]},"counts_by_year":[{"year":2019,"cited_by_count":1},{"year":2015,"cited_by_count":1}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}