{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T15:34:42Z","timestamp":1791473682040,"version":"4.3.4"},"reference-count":50,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2024,1,26]],"date-time":"2024-01-26T00:00:00Z","timestamp":1706227200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2024,5,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Since the chemical industry is largely dependent on petrol\u2010based feedstocks, new sources are required for a sustainable industry. Conversion of biomass to high\u2010value compounds provides an environmentally friendly and sustainable approach, which might be a potential solution to reduce petrol\u2010based starting materials. This also applies for <jats:italic>N<\/jats:italic>\u2010heterocycles, which are a common structural motif in natural products, pharmaceuticals and functional polymers. The synthesis of pyrroles is a well\u2010studied and established process. Nevertheless, most routes described are not in line with the principles of green and sustainable chemistry and employ harsh reaction conditions and harmful solvents. In this study, 3,4\u2010dihydroxyketons are used as excellent platform chemicals for the production of <jats:italic>N<\/jats:italic>\u2010substituted pyrrole\u20102\u2010carboxylic\u2010 and pyrrole\u20102,5\u2010dicarboxylic acids, as they can be prepared from glucose through the intermediate <jats:sc>d<\/jats:sc>\u2010glucarate and converted into pyrrolic acid derivatives under mild conditions in water. The scope of this so far unknown reaction was examined using a variety of primary amines and aqueous ammonium chloride leading to pyrrolic acid derivatives with <jats:italic>N<\/jats:italic>\u2010substituents like alkane\u2010, alkene\u2010, phenyl\u2010 and alcohol\u2010groups with yields up to 20\u2009%. The combination of both, enzymatic conversion and chemical reaction opens up new possibilities for further process development. Therefore, a continuous chemo\u2010enzymatic system was set up by first employing an immobilized enzyme to catalyze the conversion of <jats:sc>d<\/jats:sc>\u2010glucarate to the 3,4\u2010dihydroxyketone, which is further converted to the pyrrolic acid derivatives by a chemical step in continuous flow.<\/jats:p>","DOI":"10.1002\/cssc.202301169","type":"journal-article","created":{"date-parts":[[2024,1,13]],"date-time":"2024-01-13T12:34:39Z","timestamp":1705149279000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["<i>N<\/i>\u2010substituted pyrrole carboxylic acid derivatives from 3,4\u2010dihydroxyketons"],"prefix":"10.1002","volume":"17","author":[{"given":"Tatjana","family":"Laudage","sequence":"first","affiliation":[{"name":"Chair of Chemistry of Biogenic Resources Campus Straubing for Biotechnology and Sustainability Technical University of Munich  Schulgasse 16 94315 Straubing Germany."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Torben","family":"H\u00fcsing","sequence":"additional","affiliation":[{"name":"Chair of Chemistry of Biogenic Resources Campus Straubing for Biotechnology and Sustainability Technical University of Munich  Schulgasse 16 94315 Straubing Germany."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Broder","family":"R\u00fchmann","sequence":"additional","affiliation":[{"name":"Chair of Chemistry of Biogenic Resources Campus Straubing for Biotechnology and Sustainability Technical University of Munich  Schulgasse 16 94315 Straubing Germany."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Barbara","family":"Beer","sequence":"additional","affiliation":[{"name":"Chair of Chemistry of Biogenic Resources Campus Straubing for Biotechnology and Sustainability Technical University of Munich  Schulgasse 16 94315 Straubing Germany."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luca","family":"Schmermund","sequence":"additional","affiliation":[{"name":"Chair of Chemistry of Biogenic Resources Campus Straubing for Biotechnology and Sustainability Technical University of Munich  Schulgasse 16 94315 Straubing Germany."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5458-9330","authenticated-orcid":false,"given":"Volker","family":"Sieber","sequence":"additional","affiliation":[{"name":"Chair of Chemistry of Biogenic Resources Campus Straubing for Biotechnology and Sustainability Technical University of Munich  Schulgasse 16 94315 Straubing Germany."},{"name":"Catalytic Research Center Technical University of Munich  Ernst-Otto-Fischer-Stra\u00dfe 1 85748 Garching Germany"},{"name":"SynBiofoundry@TUM Technical University of Munich  Schulgasse 22 94315 Straubing Germany"},{"name":"School of Chemistry and Molecular Biosciences The University of Queensland  68 Copper Road St. Lucia 4072 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,1,26]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsps.2018.07.011"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-004-1733-0"},{"key":"e_1_2_8_3_1","unstructured":"\u00a0"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1114736"},{"key":"e_1_2_8_5_2","volume-title":"Top Value Added Chemicals from Biomass: Volume I \u2013 Results of Screening for Potential Candidates from Sugars and Synthesis Gas","author":"Werpy T.","year":"2004"},{"key":"e_1_2_8_6_1","unstructured":"\u00a0"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.iecr.7b01571"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)83292-9"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.00973-08"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.12.017"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1557\/adv.2017.181"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2012.08.017"},{"key":"e_1_2_8_13_1","unstructured":"\u00a0"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.electacta.2012.03.064"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/elan.201800044"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apsusc.2017.08.093"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801426"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202016364"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18850180290"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18850180154"},{"key":"e_1_2_8_21_1","unstructured":"\u00a0"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1080\/01614940.2018.1529932"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.gresc.2022.06.004"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.03.012"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.744"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25407g"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201501223"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC01523A"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810555"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03081"},{"key":"e_1_2_8_31_1","unstructured":"\u00a0"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b01349"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201800171"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ymben.2017.02.011"},{"key":"e_1_2_8_35_1","unstructured":"\u00a0"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b01276"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tibtech.2011.01.005"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2014.03.002"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12896-016-0308-3"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201300332"},{"key":"e_1_2_8_41_1","unstructured":"\u00a0"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ed064p591"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19301880102"},{"key":"e_1_2_8_44_1","unstructured":"\u00a0"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja905196n"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja910608m"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1142\/S021963361350017X"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2020.00585"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19515710107"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)00479-3"}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.202301169","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T17:31:56Z","timestamp":1760376716000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.202301169"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,26]]},"references-count":50,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2024,5,8]]}},"alternative-id":["10.1002\/cssc.202301169"],"URL":"https:\/\/doi.org\/10.1002\/cssc.202301169","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1,26]]},"assertion":[{"value":"2023-08-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-01-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202301169"}}