{"id":"https://openalex.org/W180603313","doi":"https://doi.org/10.1515/znc-1987-0416","title":"Enzymatic Synthesis of Riboflavin and FMN Specifically Labeled with 13C in the Xylene Ring","display_name":"Enzymatic Synthesis of Riboflavin and FMN Specifically Labeled with 13C in the Xylene Ring","publication_year":1987,"publication_date":"1987-04-01","ids":{"openalex":"https://openalex.org/W180603313","doi":"https://doi.org/10.1515/znc-1987-0416","mag":"180603313","pmid":"https://pubmed.ncbi.nlm.nih.gov/2955589"},"language":"en","primary_location":{"id":"doi:10.1515/znc-1987-0416","doi":"https://doi.org/10.1515/znc-1987-0416","is_oa":true,"landing_page_url":"https://doi.org/10.1515/znc-1987-0416","pdf_url":"https://www.degruyter.com/document/doi/10.1515/znc-1987-0416/pdf","source":{"id":"https://openalex.org/S67401564","display_name":"Zeitschrift f\u00fcr Naturforschung C","issn_l":"0341-0471","issn":["0341-0471","0939-5075","1865-7125"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-d","jufo-1","medline","norway-1","poland-40","russia-white-list-3"],"host_organization":"https://openalex.org/P4310313990","host_organization_name":"De Gruyter","host_organization_lineage":["https://openalex.org/P4310313990"],"host_organization_lineage_names":["De Gruyter"],"type":"journal"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Zeitschrift f\u00fcr Naturforschung C","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://www.degruyter.com/document/doi/10.1515/znc-1987-0416/pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5079486021","display_name":"Helmut Sedlmaier","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I62916508","display_name":"Technical University of Munich","ror":"https://ror.org/02kkvpp62","country_code":"DE","type":"education","lineage":["https://openalex.org/I62916508"]}],"countries":["DE"],"is_corresponding":false,"raw_author_name":"Helmut Sedlmaier","raw_affiliation_strings":["Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstra\u00dfe 4, D-8046 Garching, Bundesrepublik Deutschland","Present address: Kreiskrankenhaus Traunstein, Station 1, D-8220 Traunstein"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstra\u00dfe 4, D-8046 Garching, Bundesrepublik Deutschland","institution_ids":["https://openalex.org/I62916508"]},{"raw_affiliation_string":"Present address: Kreiskrankenhaus Traunstein, Station 1, D-8220 Traunstein","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5002630852","display_name":"Franz M\u00fcller","orcid":"https://orcid.org/0000-0002-8876-5643","observed_orcids":["https://orcid.org/0000-0002-8876-5643","https://orcid.org/0000-0002-6564-9121"]},"institutions":[{"id":"https://openalex.org/I913481162","display_name":"Wageningen University & Research","ror":"https://ror.org/04qw24q55","country_code":"NL","type":"education","lineage":["https://openalex.org/I913481162"]}],"countries":["NL"],"is_corresponding":false,"raw_author_name":"Franz M\u00fcller","raw_affiliation_strings":["Department of Biochemistry, Agricultural University, De Dreijen 11, 6703 BC Wageningen, The Netherlands"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Biochemistry, Agricultural University, De Dreijen 11, 6703 BC Wageningen, The Netherlands","institution_ids":["https://openalex.org/I913481162"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5109871633","display_name":"Paul J. Keller","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1324766304","display_name":"Barrow Neurological Institute","ror":"https://ror.org/01fwrsq33","country_code":"US","type":"healthcare","lineage":["https://openalex.org/I1324766304","https://openalex.org/I1325481341","https://openalex.org/I2802827176"]},{"id":"https://openalex.org/I62916508","display_name":"Technical University of Munich","ror":"https://ror.org/02kkvpp62","country_code":"DE","type":"education","lineage":["https://openalex.org/I62916508"]}],"countries":["DE","US"],"is_corresponding":false,"raw_author_name":"Paul J. Keller","raw_affiliation_strings":["Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstra\u00dfe 4, D-8046 Garching, Bundesrepublik Deutschland","Present address: Barrow Neurological Institute, St. Joseph\u2019s Hospital, 350 West Thomas Road, Phoenix, Arizona 85013-4496, USA","Present address: Kreiskrankenhaus Traunstein, Station 1, D-8220 Traunstein"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstra\u00dfe 4, D-8046 Garching, Bundesrepublik Deutschland","institution_ids":["https://openalex.org/I62916508"]},{"raw_affiliation_string":"Present address: Barrow Neurological Institute, St. Joseph\u2019s Hospital, 350 West Thomas Road, Phoenix, Arizona 85013-4496, USA","institution_ids":["https://openalex.org/I1324766304"]},{"raw_affiliation_string":"Present address: Kreiskrankenhaus Traunstein, Station 1, D-8220 Traunstein","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5068798153","display_name":"Adelbert Bacher","orcid":"https://orcid.org/0000-0001-5174-4139","observed_orcids":["https://orcid.org/0000-0001-5174-4139"]},"institutions":[{"id":"https://openalex.org/I913481162","display_name":"Wageningen University & Research","ror":"https://ror.org/04qw24q55","country_code":"NL","type":"education","lineage":["https://openalex.org/I913481162"]}],"countries":["NL"],"is_corresponding":false,"raw_author_name":"Adelbert Bacher","raw_affiliation_strings":["Department of Biochemistry, Agricultural University, De Dreijen 11, 6703 BC Wageningen, The Netherlands"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Biochemistry, Agricultural University, De Dreijen 11, 6703 BC Wageningen, The Netherlands","institution_ids":["https://openalex.org/I913481162"]}]}],"institutions":[],"countries_distinct_count":3,"institutions_distinct_count":3,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":2400,"currency":"EUR","value_usd":2712},"apc_paid":{"value":2400,"currency":"EUR","value_usd":2712},"fwci":1.0274,"has_fulltext":true,"cited_by_count":51,"citation_normalized_percentile":{"value":0.6649635,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"42","issue":"4","first_page":"425","last_page":"429"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13561","display_name":"Chemical Reactions and Isotopes","score":0.7943999767303467,"subfield":{"id":"https://openalex.org/subfields/3003","display_name":"Pharmaceutical Science"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T13561","display_name":"Chemical Reactions and Isotopes","score":0.7943999767303467,"subfield":{"id":"https://openalex.org/subfields/3003","display_name":"Pharmaceutical Science"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T11809","display_name":"Advanced NMR Techniques and Applications","score":0.1437000036239624,"subfield":{"id":"https://openalex.org/subfields/1607","display_name":"Spectroscopy"},"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/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.010999999940395355,"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/riboflavin","display_name":"riboflavin","score":0.9419999718666077},{"id":"https://openalex.org/keywords/flavin-mononucleotide","display_name":"flavin mononucleotide","score":0.8330000042915344},{"id":"https://openalex.org/keywords/13c-labeling","display_name":"13C labeling","score":0.7839999794960022},{"id":"https://openalex.org/keywords/enzymatic-synthesis","display_name":"enzymatic synthesis","score":0.7649999856948853},{"id":"https://openalex.org/keywords/riboflavin-synthase","display_name":"riboflavin synthase","score":0.9629999995231628},{"id":"https://openalex.org/keywords/lumazine","display_name":"lumazine","score":0.5509999990463257},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.9129999876022339},{"id":"https://openalex.org/keywords/diacetyl","display_name":"diacetyl","score":0.6110000014305115},{"id":"https://openalex.org/keywords/phosphorylation","display_name":"phosphorylation","score":0.6610000133514404},{"id":"https://openalex.org/keywords/riboflavin-biosynthesis","display_name":"riboflavin biosynthesis","score":0.5490000247955322}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9115945100784302},{"id":"https://openalex.org/C2776155809","wikidata":"https://www.wikidata.org/wiki/Q130365","display_name":"Riboflavin","level":2,"score":0.746462881565094},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.7291271686553955},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.6847564578056335},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.5787549018859863},{"id":"https://openalex.org/C2776568683","wikidata":"https://www.wikidata.org/wiki/Q23005640","display_name":"Moiety","level":2,"score":0.5373424887657166},{"id":"https://openalex.org/C2776203871","wikidata":"https://www.wikidata.org/wiki/Q83187","display_name":"Thiamine","level":2,"score":0.5070054531097412},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.43183478713035583},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.3265933394432068},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2781842350959778},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.14882776141166687},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.13795754313468933},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D001412","descriptor_name":"Bacillus subtilis","qualifier_ui":"Q000201","qualifier_name":"enzymology","is_major_topic":false},{"descriptor_ui":"D002247","descriptor_name":"Carbon Isotopes","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005486","descriptor_name":"Flavin Mononucleotide","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D007202","descriptor_name":"Indicators and Reagents","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007553","descriptor_name":"Isotope Labeling","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false},{"descriptor_ui":"D012256","descriptor_name":"Riboflavin","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D012258","descriptor_name":"Riboflavin Synthase","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false}],"locations_count":4,"locations":[{"id":"doi:10.1515/znc-1987-0416","doi":"https://doi.org/10.1515/znc-1987-0416","is_oa":true,"landing_page_url":"https://doi.org/10.1515/znc-1987-0416","pdf_url":"https://www.degruyter.com/document/doi/10.1515/znc-1987-0416/pdf","source":{"id":"https://openalex.org/S67401564","display_name":"Zeitschrift f\u00fcr Naturforschung C","issn_l":"0341-0471","issn":["0341-0471","0939-5075","1865-7125"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-d","jufo-1","medline","norway-1","poland-40","russia-white-list-3"],"host_organization":"https://openalex.org/P4310313990","host_organization_name":"De Gruyter","host_organization_lineage":["https://openalex.org/P4310313990"],"host_organization_lineage_names":["De Gruyter"],"type":"journal"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Zeitschrift f\u00fcr Naturforschung C","raw_type":"journal-article"},{"id":"pmid:2955589","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/2955589","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":"Zeitschrift fur Naturforschung. C, Journal of biosciences","raw_type":"Journal Article"},{"id":"pmh:oai:library.wur.nl:wurpubs/2617","doi":null,"is_oa":true,"landing_page_url":"https://research.wur.nl/en/publications/enzymatic-synthesis-of-riboflavin-and-fmn-specifically-labeled-wi","pdf_url":null,"source":{"id":"https://openalex.org/S4210201231","display_name":"Socio-Environmental Systems Modeling","issn_l":"2663-3027","issn":["2663-3027"],"is_oa":true,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core"],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"journal"},"license":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"ISSN: 0939-5075","raw_type":"Article/Letter to editor"},{"id":"pmh:wur:oai:library.wur.nl:wurpubs/2617","doi":null,"is_oa":false,"landing_page_url":"https://research.wur.nl/en/publications/enzymatic-synthesis-of-riboflavin-and-fmn-specifically-labeled-wi","pdf_url":null,"source":{"id":"https://openalex.org/S4306401843","display_name":"Data Archiving and Networked Services (DANS)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1322597698","host_organization_name":"Royal Netherlands Academy of Arts and Sciences","host_organization_lineage":["https://openalex.org/I1322597698"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Zeitschrift f\u00fcr Naturforschung. Section C : a Journal of Biosciences, 42, 425 - 429","raw_type":"info:eu-repo/semantics/article"}],"best_oa_location":{"id":"doi:10.1515/znc-1987-0416","doi":"https://doi.org/10.1515/znc-1987-0416","is_oa":true,"landing_page_url":"https://doi.org/10.1515/znc-1987-0416","pdf_url":"https://www.degruyter.com/document/doi/10.1515/znc-1987-0416/pdf","source":{"id":"https://openalex.org/S67401564","display_name":"Zeitschrift f\u00fcr Naturforschung C","issn_l":"0341-0471","issn":["0341-0471","0939-5075","1865-7125"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-d","jufo-1","medline","norway-1","poland-40","russia-white-list-3"],"host_organization":"https://openalex.org/P4310313990","host_organization_name":"De Gruyter","host_organization_lineage":["https://openalex.org/P4310313990"],"host_organization_lineage_names":["De Gruyter"],"type":"journal"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Zeitschrift f\u00fcr Naturforschung C","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":true,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W180603313.pdf","grobid_xml":"https://content.openalex.org/works/W180603313.grobid-xml"},"referenced_works_count":5,"referenced_works":["https://openalex.org/W606135545","https://openalex.org/W4241822117","https://openalex.org/W6625755883","https://openalex.org/W6634118955","https://openalex.org/W6819780899"],"related_works":["https://openalex.org/W98465441","https://openalex.org/W2012145688","https://openalex.org/W2087892733","https://openalex.org/W1039779313","https://openalex.org/W2089961627","https://openalex.org/W2019904500","https://openalex.org/W1978447630","https://openalex.org/W2144982251","https://openalex.org/W3163191957","https://openalex.org/W1581942917"],"abstract_inverted_index":{"The":[0,74],"condensation":[1,69],"of":[2,18,26,42,49,70,95,99],"3-hydroximino-2-butanone":[3],"(1)":[4],"with":[5,22,36,72,86,105],"5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione":[6],"(2)":[7],"yields":[8,111],"6,7-dimethyl-8-ribityllumazine":[9],"(3).":[10],"At":[11],"slightly":[12],"alkaline":[13],"pH,":[14],"the":[15,23,33,82,96,112],"carbonyl":[16],"group":[17,25],"1":[19,50],"reacts":[20],"preferentially":[21],"5-amino":[24],"2":[27,71],"(regioselectivity,":[28],"4:1).":[29],"Under":[30],"acidic":[31],"conditions,":[32],"reaction":[34],"occurs":[35],"higher":[37],"yield":[38],"and":[39],"marginal":[40],"regioselectivity":[41],"opposite":[43],"direction":[44],"(1:1.4).":[45],"Appropriately":[46],"13C-labeled":[47,114],"samples":[48],"afford":[51],"3":[52,76],"labeled":[53,104],"at":[54,107],"C-6":[55],"alpha,":[56,63],"C-6,":[57],"C-7":[58,60],"or":[59],"alpha.":[61],"[6":[62],"7":[64],"alpha-13C2]-3":[65],"was":[66],"prepared":[67],"by":[68,81],"[1,4-13C2]diacetyl.":[73],"lumazines":[75],"were":[77],"converted":[78],"to":[79],"riboflavin":[80,84,100],"enzyme,":[83],"synthase,":[85],"almost":[87],"quantitative":[88],"yield.":[89],"By":[90],"this":[91],"procedure,":[92],"any":[93],"C-atom":[94],"carbocyclic":[97],"moiety":[98],"can":[101],"be":[102],"selectively":[103],"13C":[106],"high":[108],"abundance.":[109],"Phosphorylation":[110],"respectively":[113],"FMN":[115],"samples.":[116]},"counts_by_year":[{"year":2023,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":3}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}