{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Pressnitz D"],"funding":["Österreichische Forschungsförderungsgesellschaft","Austrian Science Fund FWF","FP7 People: Marie-Curie Actions","Austrian Centre of Industrial Biotechnology"],"pagination":["10683-10687"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC6146909"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["57(33)"],"pubmed_abstract":["Stereoselective methods for the synthesis of tetrahydro-ß-carbolines are of significant interest due to the broad spectrum of biological activity of the target molecules. In the plant kingdom, strictosidine synthases catalyze the C-C coupling through a Pictet-Spengler reaction of tryptamine and secologanin to exclusively form the (S)-configured tetrahydro-ß-carboline (S)-strictosidine. Investigating the biocatalytic Pictet-Spengler reaction of tryptamine with small-molecular-weight aliphatic aldehydes revealed that the strictosidine synthases give unexpectedly access to the (R)-configured product. Developing an efficient expression method for the enzyme allowed the preparative transformation of various aldehydes, giving the products with up to >98 % ee. With this tool in hand, a chemoenzymatic two-step synthesis of (R)-harmicine was achieved, giving (R)-harmicine in 67 % overall yield in optically pure form."],"journal":["Angewandte Chemie (International ed. in English)"],"pubmed_title":["Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-ß-carbolines Catalyzed by Strictosidine Synthases."],"pmcid":["PMC6146909"],"funding_grant_id":["project W9-01, DK Molecular Enzymology","acib","grant agreement #289646"],"pubmed_authors":["Fischereder EM","Kroutil W","Kofler C","Hammerer L","Lechner H","Richter N","Pletz J","Hiebler K","Pressnitz D","Eger E"],"additional_accession":[]},"is_claimable":false,"name":"Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-ß-carbolines Catalyzed by Strictosidine Synthases.","description":"Stereoselective methods for the synthesis of tetrahydro-ß-carbolines are of significant interest due to the broad spectrum of biological activity of the target molecules. In the plant kingdom, strictosidine synthases catalyze the C-C coupling through a Pictet-Spengler reaction of tryptamine and secologanin to exclusively form the (S)-configured tetrahydro-ß-carboline (S)-strictosidine. Investigating the biocatalytic Pictet-Spengler reaction of tryptamine with small-molecular-weight aliphatic aldehydes revealed that the strictosidine synthases give unexpectedly access to the (R)-configured product. Developing an efficient expression method for the enzyme allowed the preparative transformation of various aldehydes, giving the products with up to >98 % ee. With this tool in hand, a chemoenzymatic two-step synthesis of (R)-harmicine was achieved, giving (R)-harmicine in 67 % overall yield in optically pure form.","dates":{"release":"2018-01-01T00:00:00Z","publication":"2018 Aug","modification":"2026-05-05T23:27:31.278Z","creation":"2019-03-26T23:57:24Z"},"accession":"S-EPMC6146909","cross_references":{"pubmed":["29852524"],"doi":["10.1002/anie.201803372"]}}