{"id":"https://openalex.org/W1996420060","doi":"https://doi.org/10.1021/jo0620967","title":"Multisite Modification of Neomycin B: Combined Mitsunobu and Click Chemistry Approach","display_name":"Multisite Modification of Neomycin B: Combined Mitsunobu and Click Chemistry Approach","publication_year":2007,"publication_date":"2007-02-14","ids":{"openalex":"https://openalex.org/W1996420060","doi":"https://doi.org/10.1021/jo0620967","mag":"1996420060","pmid":"https://pubmed.ncbi.nlm.nih.gov/17298096"},"language":"en","primary_location":{"id":"doi:10.1021/jo0620967","doi":"https://doi.org/10.1021/jo0620967","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo0620967","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/A5075887548","display_name":"Sabina Quader","orcid":"https://orcid.org/0000-0002-9616-7408","observed_orcids":["https://orcid.org/0000-0002-9616-7408"]},"institutions":[{"id":"https://openalex.org/I11701301","display_name":"Griffith University","ror":"https://ror.org/02sc3r913","country_code":"AU","type":"education","lineage":["https://openalex.org/I11701301"]}],"countries":["AU"],"is_corresponding":false,"raw_author_name":"Sabina Quader","raw_affiliation_strings":["Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia","institution_ids":["https://openalex.org/I11701301"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5039456580","display_name":"Sue E. Boyd","orcid":"https://orcid.org/0000-0003-1086-8973","observed_orcids":["https://orcid.org/0000-0003-1086-8973"]},"institutions":[{"id":"https://openalex.org/I11701301","display_name":"Griffith University","ror":"https://ror.org/02sc3r913","country_code":"AU","type":"education","lineage":["https://openalex.org/I11701301"]}],"countries":["AU"],"is_corresponding":false,"raw_author_name":"Sue E. Boyd","raw_affiliation_strings":["Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia","institution_ids":["https://openalex.org/I11701301"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5011490261","display_name":"Ian D. Jenkins","orcid":"https://orcid.org/0000-0003-3961-2277","observed_orcids":["https://orcid.org/0000-0003-3961-2277"]},"institutions":[{"id":"https://openalex.org/I11701301","display_name":"Griffith University","ror":"https://ror.org/02sc3r913","country_code":"AU","type":"education","lineage":["https://openalex.org/I11701301"]}],"countries":["AU"],"is_corresponding":false,"raw_author_name":"Ian D. Jenkins","raw_affiliation_strings":["Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia","institution_ids":["https://openalex.org/I11701301"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5005114644","display_name":"Todd A. Houston","orcid":"https://orcid.org/0000-0001-9369-8804","observed_orcids":["https://orcid.org/0000-0001-9369-8804"]},"institutions":[{"id":"https://openalex.org/I11701301","display_name":"Griffith University","ror":"https://ror.org/02sc3r913","country_code":"AU","type":"education","lineage":["https://openalex.org/I11701301"]}],"countries":["AU"],"is_corresponding":false,"raw_author_name":"Todd A. Houston","raw_affiliation_strings":["Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Eskitis Institute and Natural Product Discovery, Griffith University, Nathan, QLD 4111, Australia, and Institute for Glycomics, Griffith University, Gold Coast, QLD 9726, Australia","institution_ids":["https://openalex.org/I11701301"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I11701301"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":5.039,"has_fulltext":false,"cited_by_count":77,"citation_normalized_percentile":{"value":0.96004132,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"72","issue":"6","first_page":"1962","last_page":"1979"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11440","display_name":"Click Chemistry and Applications","score":0.47609999775886536,"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/T11440","display_name":"Click Chemistry and Applications","score":0.47609999775886536,"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/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.3562000095844269,"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/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.02889999933540821,"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/neomycin-b","display_name":"neomycin B","score":1.0},{"id":"https://openalex.org/keywords/aminoglycosides","display_name":"aminoglycosides","score":0.8659999966621399},{"id":"https://openalex.org/keywords/mitsunobu-reaction","display_name":"Mitsunobu reaction","score":0.9580000042915344},{"id":"https://openalex.org/keywords/click-chemistry","display_name":"click chemistry","score":0.8920000195503235},{"id":"https://openalex.org/keywords/aziridine-formation","display_name":"aziridine formation","score":0.7559999823570251},{"id":"https://openalex.org/keywords/epoxide-ring-opening","display_name":"epoxide ring opening","score":0.859000027179718},{"id":"https://openalex.org/keywords/neighboring-group-effects","display_name":"neighboring group effects","score":0.6690000295639038},{"id":"https://openalex.org/keywords/conformational-analysis","display_name":"conformational analysis","score":0.8119999766349792}],"concepts":[{"id":"https://openalex.org/C2778544067","wikidata":"https://www.wikidata.org/wiki/Q409141","display_name":"Aziridine","level":3,"score":0.9626774787902832},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9097254276275635},{"id":"https://openalex.org/C2776920199","wikidata":"https://www.wikidata.org/wiki/Q408028","display_name":"Epoxide","level":3,"score":0.7940347194671631},{"id":"https://openalex.org/C2779377163","wikidata":"https://www.wikidata.org/wiki/Q899062","display_name":"Mitsunobu reaction","level":2,"score":0.7694429755210876},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.7335312366485596},{"id":"https://openalex.org/C2779841869","wikidata":"https://www.wikidata.org/wiki/Q423098","display_name":"Neomycin","level":3,"score":0.6729820370674133},{"id":"https://openalex.org/C18705241","wikidata":"https://www.wikidata.org/wiki/Q1128023","display_name":"Conformational isomerism","level":3,"score":0.6343608498573303},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5773622393608093},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3867274820804596},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.18582943081855774},{"id":"https://openalex.org/C501593827","wikidata":"https://www.wikidata.org/wiki/Q12187","display_name":"Antibiotics","level":2,"score":0.1857793629169464},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.18347600102424622},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.06850281357765198},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D001388","descriptor_name":"Aziridines","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005601","descriptor_name":"Framycetin","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1021/jo0620967","doi":"https://doi.org/10.1021/jo0620967","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo0620967","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:17298096","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/17298096","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"},{"id":"pmh:oai:research-repository.griffith.edu.au:10072/17941","doi":null,"is_oa":false,"landing_page_url":"http://hdl.handle.net/10072/17941","pdf_url":null,"source":{"id":"https://openalex.org/S7407064376","display_name":"Griffith Research Online","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"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":33,"referenced_works":["https://openalex.org/W1548364374","https://openalex.org/W1968652549","https://openalex.org/W1976080873","https://openalex.org/W1981573250","https://openalex.org/W1984582584","https://openalex.org/W1985684677","https://openalex.org/W2012416622","https://openalex.org/W2016492689","https://openalex.org/W2018429609","https://openalex.org/W2029772790","https://openalex.org/W2037699558","https://openalex.org/W2047261853","https://openalex.org/W2048177811","https://openalex.org/W2053035864","https://openalex.org/W2067214581","https://openalex.org/W2068680026","https://openalex.org/W2073127984","https://openalex.org/W2093649670","https://openalex.org/W2101250552","https://openalex.org/W2105225694","https://openalex.org/W2108225803","https://openalex.org/W2113188290","https://openalex.org/W2114822734","https://openalex.org/W2142437557","https://openalex.org/W2145662716","https://openalex.org/W2146444740","https://openalex.org/W2155373804","https://openalex.org/W2159192805","https://openalex.org/W2316250907","https://openalex.org/W3151144641","https://openalex.org/W4249568576","https://openalex.org/W4250544746","https://openalex.org/W4256183050"],"related_works":["https://openalex.org/W1976080873","https://openalex.org/W2018171686","https://openalex.org/W2782328958","https://openalex.org/W2072978224","https://openalex.org/W1979671685","https://openalex.org/W2073181000","https://openalex.org/W2052624408","https://openalex.org/W2017382951","https://openalex.org/W2327355177","https://openalex.org/W1987971818"],"abstract_inverted_index":{"The":[0],"aminoglycoside":[1],"antibiotic":[2],"neomycin":[3,98,121],"B":[4],"has":[5],"been":[6],"converted":[7],"into":[8],"several":[9],"novel":[10],"building":[11,99],"blocks":[12,100],"that":[13],"can":[14,35,101,125],"be":[15,36,102,127],"used":[16,37],"for":[17],"the":[18,24,32,41,46,55,75,79,87,94],"specific":[19],"modification":[20],"of":[21,23,78,119],"three":[22],"four":[25],"ring":[26,43,58,81,89],"systems.":[27,148],"Under":[28],"carefully":[29],"controlled":[30],"conditions,":[31,54],"Mitsunobu":[33,60],"reaction":[34],"to":[38,44,62,108,115,132],"selectively":[39],"dehydrate":[40],"ido":[42],"give":[45,63],"talo":[47],"epoxide.":[48],"Subsequently":[49],"however,":[50],"under":[51],"more":[52],"forcing":[53],"2-deoxy":[56],"streptamine":[57],"undergoes":[59],"dehydration":[61],"an":[64],"aziridine.":[65],"An":[66],"unusual":[67],"remote":[68],"neighboring":[69],"group":[70],"effect":[71],"was":[72,82],"observed.":[73],"When":[74],"primary":[76],"hydroxyl":[77],"ribose":[80],"blocked,":[83],"aziridine":[84],"formation":[85],"on":[86],"deoxystreptamine":[88],"did":[90],"not":[91],"occur.":[92],"Both":[93],"epoxide":[95],"and":[96,106],"epoxide-aziridine":[97],"ring-opened":[103],"with":[104,112],"azide":[105],"subjected":[107],"\"click\"":[109],"type":[110],"chemistry":[111],"terminal":[113],"alkynes":[114],"generate":[116],"a":[117],"series":[118],"new":[120],"analogues.":[122],"These":[123],"reactions":[124],"all":[126],"carried":[128],"out":[129],"without":[130],"recourse":[131],"O-protecting":[133],"groups.":[134],"A":[135],"detailed":[136],"conformational":[137],"analysis":[138],"by":[139],"NMR":[140],"revealed":[141],"some":[142],"unexpected":[143],"conformer":[144],"preferences":[145],"in":[146],"these":[147]},"counts_by_year":[{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":3},{"year":2021,"cited_by_count":2},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":5},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":5},{"year":2015,"cited_by_count":5},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":6},{"year":2012,"cited_by_count":6}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}