{"id":"https://openalex.org/W3202374318","doi":"https://doi.org/10.1021/acs.orglett.1c02974","title":"Micromonosporamide A with Glutamine-Dependent Cytotoxicity from Micromonospora sp. MM609M-173N6: Isolation, Stereochemical Determination, and Synthesis","display_name":"Micromonosporamide A with Glutamine-Dependent Cytotoxicity from Micromonospora sp. MM609M-173N6: Isolation, Stereochemical Determination, and Synthesis","publication_year":2021,"publication_date":"2021-09-29","ids":{"openalex":"https://openalex.org/W3202374318","doi":"https://doi.org/10.1021/acs.orglett.1c02974","mag":"3202374318","pmid":"https://pubmed.ncbi.nlm.nih.gov/34585936"},"language":"en","primary_location":{"id":"doi:10.1021/acs.orglett.1c02974","doi":"https://doi.org/10.1021/acs.orglett.1c02974","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.1c02974","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"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/A5065727500","display_name":"Toshifumi Takeuchi","orcid":"https://orcid.org/0000-0002-5096-0857","observed_orcids":["https://orcid.org/0000-0002-5096-0857"]},"institutions":[{"id":"https://openalex.org/I4210111963","display_name":"Microbial Chemistry Research Foundation","ror":"https://ror.org/02bwxve09","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210111963"]}],"countries":["JP"],"is_corresponding":true,"raw_author_name":"Toshifumi Takeuchi","raw_affiliation_strings":["Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan"],"raw_orcid":"https://orcid.org/0000-0002-5096-0857","affiliations":[{"raw_affiliation_string":"Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan","institution_ids":["https://openalex.org/I4210111963"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5103125714","display_name":"Masaki Hatano","orcid":"https://orcid.org/0000-0002-9602-6197","observed_orcids":["https://orcid.org/0000-0002-9602-6197"]},"institutions":[{"id":"https://openalex.org/I4210111963","display_name":"Microbial Chemistry Research Foundation","ror":"https://ror.org/02bwxve09","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210111963"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Masaki Hatano","raw_affiliation_strings":["Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan","institution_ids":["https://openalex.org/I4210111963"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5052083115","display_name":"Hideyuki Muramatsu","orcid":"https://orcid.org/0000-0001-5900-2113","observed_orcids":["https://orcid.org/0000-0001-5900-2113"]},"institutions":[{"id":"https://openalex.org/I4210111963","display_name":"Microbial Chemistry Research Foundation","ror":"https://ror.org/02bwxve09","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210111963"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Hideyuki Muramatsu","raw_affiliation_strings":["Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan","institution_ids":["https://openalex.org/I4210111963"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Yumiko Kubota","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210111963","display_name":"Microbial Chemistry Research Foundation","ror":"https://ror.org/02bwxve09","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210111963"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Yumiko Kubota","raw_affiliation_strings":["Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan","institution_ids":["https://openalex.org/I4210111963"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5035057394","display_name":"Ry\u00fbichi Sawa","orcid":"https://orcid.org/0000-0002-8190-0195","observed_orcids":["https://orcid.org/0000-0002-8190-0195"]},"institutions":[{"id":"https://openalex.org/I4210111963","display_name":"Microbial Chemistry Research Foundation","ror":"https://ror.org/02bwxve09","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210111963"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Ryuichi Sawa","raw_affiliation_strings":["Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan","institution_ids":["https://openalex.org/I4210111963"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5059777922","display_name":"Masayuki Igarashi","orcid":"https://orcid.org/0000-0002-1562-6685","observed_orcids":["https://orcid.org/0000-0002-1562-6685"]},"institutions":[{"id":"https://openalex.org/I4210111963","display_name":"Microbial Chemistry Research Foundation","ror":"https://ror.org/02bwxve09","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210111963"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Masayuki Igarashi","raw_affiliation_strings":["Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan","institution_ids":["https://openalex.org/I4210111963"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5065727500"],"corresponding_institution_ids":["https://openalex.org/I4210111963"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":0.4214,"has_fulltext":false,"cited_by_count":4,"citation_normalized_percentile":{"value":0.46992754,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":95},"biblio":{"volume":"23","issue":"20","first_page":"7981","last_page":"7985"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10252","display_name":"Microbial Natural Products and Biosynthesis","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/2402","display_name":"Applied Microbiology and Biotechnology"},"field":{"id":"https://openalex.org/fields/24","display_name":"Immunology and Microbiology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T10252","display_name":"Microbial Natural Products and Biosynthesis","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/2402","display_name":"Applied Microbiology and Biotechnology"},"field":{"id":"https://openalex.org/fields/24","display_name":"Immunology and Microbiology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T11340","display_name":"Marine Sponges and Natural Products","score":0.00019999999494757503,"subfield":{"id":"https://openalex.org/subfields/1305","display_name":"Biotechnology"},"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/T13971","display_name":"Isoquinoline Alkaloid Synthesis","score":0.00019999999494757503,"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/micromonospora","display_name":"Micromonospora","score":0.9089999794960022},{"id":"https://openalex.org/keywords/structure-elucidation","display_name":"structure elucidation","score":0.7350000143051147},{"id":"https://openalex.org/keywords/absolute-configuration","display_name":"absolute configuration","score":0.7689999938011169},{"id":"https://openalex.org/keywords/marfey-s-method","display_name":"Marfey's method","score":0.8339999914169312},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.9120000004768372},{"id":"https://openalex.org/keywords/natural-product-isolation","display_name":"natural product isolation","score":0.6840000152587891},{"id":"https://openalex.org/keywords/antiproliferative-activity","display_name":"antiproliferative activity","score":0.8980000019073486},{"id":"https://openalex.org/keywords/stereochemistry","display_name":"stereochemistry","score":0.31299999356269836}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8861260414123535},{"id":"https://openalex.org/C162356407","wikidata":"https://www.wikidata.org/wiki/Q180809","display_name":"Mass spectrometry","level":2,"score":0.6635933518409729},{"id":"https://openalex.org/C97428945","wikidata":"https://www.wikidata.org/wiki/Q15305109","display_name":"Fractionation","level":2,"score":0.6163266897201538},{"id":"https://openalex.org/C43617362","wikidata":"https://www.wikidata.org/wiki/Q170050","display_name":"Chromatography","level":1,"score":0.5833495855331421},{"id":"https://openalex.org/C2779349466","wikidata":"https://www.wikidata.org/wiki/Q181619","display_name":"Glutamine","level":3,"score":0.5674750804901123},{"id":"https://openalex.org/C25170562","wikidata":"https://www.wikidata.org/wiki/Q2052053","display_name":"Absolute configuration","level":2,"score":0.5652202367782593},{"id":"https://openalex.org/C2781382891","wikidata":"https://www.wikidata.org/wiki/Q3061522","display_name":"Micromonospora","level":4,"score":0.5498462319374084},{"id":"https://openalex.org/C138268822","wikidata":"https://www.wikidata.org/wiki/Q1051925","display_name":"Resolution (logic)","level":2,"score":0.42958009243011475},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.40366971492767334},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.169683039188385},{"id":"https://openalex.org/C523546767","wikidata":"https://www.wikidata.org/wiki/Q10876","display_name":"Bacteria","level":2,"score":0.15184113383293152},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.12160536646842957},{"id":"https://openalex.org/C2779920670","wikidata":"https://www.wikidata.org/wiki/Q1144013","display_name":"Streptomyces","level":3,"score":0.0},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.0},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.0},{"id":"https://openalex.org/C154945302","wikidata":"https://www.wikidata.org/wiki/Q11660","display_name":"Artificial intelligence","level":1,"score":0.0},{"id":"https://openalex.org/C54355233","wikidata":"https://www.wikidata.org/wiki/Q7162","display_name":"Genetics","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000302","qualifier_name":"isolation & purification","is_major_topic":false},{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D004151","descriptor_name":"Dipeptides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D005285","descriptor_name":"Fermentation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005973","descriptor_name":"Glutamine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D008847","descriptor_name":"Micromonospora","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D008847","descriptor_name":"Micromonospora","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/acs.orglett.1c02974","doi":"https://doi.org/10.1021/acs.orglett.1c02974","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.1c02974","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","raw_type":"journal-article"},{"id":"pmid:34585936","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/34585936","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":"Organic letters","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G6164338410","display_name":"Screening of glutaminolysis or glutamine metabolism inhibitors","funder_award_id":"19K05726","funder_id":"https://openalex.org/F4320334764","funder_display_name":"Japan Society for the Promotion of Science"}],"funders":[{"id":"https://openalex.org/F4320334764","display_name":"Japan Society for the Promotion of Science","ror":"https://ror.org/00hhkn466"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":25,"referenced_works":["https://openalex.org/W184122029","https://openalex.org/W1973304708","https://openalex.org/W1980756616","https://openalex.org/W1987304313","https://openalex.org/W2015700848","https://openalex.org/W2019135498","https://openalex.org/W2036255336","https://openalex.org/W2047503922","https://openalex.org/W2067499871","https://openalex.org/W2077781738","https://openalex.org/W2083471799","https://openalex.org/W2093361250","https://openalex.org/W2143271842","https://openalex.org/W2150610836","https://openalex.org/W2323361621","https://openalex.org/W2326842020","https://openalex.org/W2327335719","https://openalex.org/W2345381093","https://openalex.org/W2474835343","https://openalex.org/W2565405666","https://openalex.org/W2732668513","https://openalex.org/W2742280164","https://openalex.org/W2810290765","https://openalex.org/W2921566297","https://openalex.org/W4242419874"],"related_works":["https://openalex.org/W2051115544","https://openalex.org/W2001464694","https://openalex.org/W2952860435","https://openalex.org/W7116869341","https://openalex.org/W2019928407","https://openalex.org/W2116146304","https://openalex.org/W2011037474","https://openalex.org/W1985233270","https://openalex.org/W1969041543","https://openalex.org/W2084250420"],"abstract_inverted_index":{"sp.":[0],"MM609M-173N6":[1],"by":[2,48],"bioassay-guided":[3],"fractionation":[4],"using":[5,41],"a":[6,42],"glutamine":[7],"compensation":[8],"assay.":[9],"The":[10,30],"planar":[11],"structure":[12],"was":[13],"elucidated":[14],"on":[15],"the":[16,36],"basis":[17],"of":[18,35],"comprehensive":[19],"one-":[20],"and":[21,26,32,55],"two-dimensional":[22],"nuclear":[23],"magnetic":[24],"resonance":[25],"high-resolution":[27],"mass":[28],"spectrometry.":[29],"relative":[31],"absolute":[33],"configuration":[34],"entire":[37],"molecule":[38],"were":[39],"determined":[40],"combined":[43],"approach,":[44],"involving":[45],"chromatographic":[46],"analysis":[47],"liquid":[49],"chromatography-mass":[50],"spectrometry,":[51],"advanced":[52],"Marfey's":[53],"method,":[54],"total":[56],"synthesis.":[57],"Micromonosporamide":[58],"A":[59],"exhibited":[60],"glutamine-dependent":[61],"antiproliferative":[62],"activity.":[63]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":1}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2021-10-11T00:00:00"}