{"corpus_id":46636477,"paper_sha":"0e39f8237060097d6fe255068ed7035455807169","doi":"10.1074/JBC.M109287200","arxiv_id":null,"pmid":11641410,"pmcid":null,"mag_id":1997613651,"dblp_id":null,"acl_id":null,"title":"The Activity of ArabidopsisGlycosyltransferases toward Salicylic Acid, 4-Hydroxybenzoic Acid, and Other Benzoates*","year":2002,"publication_date":"2002-01-04","venue":"Journal of Biological Chemistry","journal":{"name":"The Journal of Biological Chemistry","pages":"586 - 592","volume":"277"},"journal_issn":null,"journal_title":null,"publication_types":["JournalArticle"],"pubmed_pub_types":["Journal Article","Research Support, Non-U.S. Gov't"],"s2_fields_of_study":["Biology","Medicine","Chemistry","Environmental Science"],"reference_count":47,"citation_count":282,"influential_citation_count":28,"is_open_access":true,"arxiv_categories":null,"arxiv_license":null,"arxiv_journal_ref":null,"mesh_headings":[{"d":"Arabidopsis","mj":false,"qs":[{"q":"enzymology","mj":true,"ui":"Q000201"}],"ui":"D017360"},{"d":"Base Sequence","mj":false,"ui":"D001483"},{"d":"Benzoates","mj":false,"qs":[{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D001565"},{"d":"Glycosyltransferases","mj":false,"qs":[{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D016695"},{"d":"Molecular Conformation","mj":false,"ui":"D008968"},{"d":"Molecular Sequence Data","mj":false,"ui":"D008969"},{"d":"Parabens","mj":false,"qs":[{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D010226"},{"d":"Salicylic Acid","mj":false,"qs":[{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D020156"},{"d":"Uridine Diphosphate Glucose","mj":false,"qs":[{"q":"metabolism","mj":false,"ui":"Q000378"}],"ui":"D014532"}],"chemicals":[{"n":"Benzoates","ui":"D001565","reg":"0"},{"n":"Parabens","ui":"D010226","reg":"0"},{"n":"Glycosyltransferases","ui":"D016695","reg":"EC 2.4.-"},{"n":"4-hydroxybenzoic acid","ui":"C038193","reg":"JG8Z55Y12H"},{"n":"Salicylic Acid","ui":"D020156","reg":"O414PZ4LPZ"},{"n":"Uridine Diphosphate Glucose","ui":"D014532","reg":"V50K1D7P4Y"}],"comments_corrections":null,"source_flags":5,"s2_open_access_pdf_url":"http://www.jbc.org/article/S002192582088048X/pdf","s2_open_access_landing_url":"https://www.semanticscholar.org/paper/0e39f8237060097d6fe255068ed7035455807169","s2_open_access_license":"CCBY","s2_open_access_status":"HYBRID","pmc_open_access_pdf_url":null,"pmc_open_access_landing_url":null,"pmc_open_access_license":null,"pmc_open_access_status":null,"unpaywall_open_access_pdf_url":null,"unpaywall_open_access_landing_url":null,"unpaywall_open_access_license":null,"unpaywall_open_access_status":null,"abstract":"Benzoates are a class of natural products containing compounds of industrial and strategic importance. In plants, the compounds exist in free form and as conjugates to a wide range of other metabolites such as glucose, which can be attached to the carboxyl group or to specific hydroxyl groups on the benzene ring. These glucosylation reactions have been studied for many years, but to date only one gene encoding a benzoate glucosyltransferase has been cloned. A phylogenetic analysis of sequences in theArabidopsis genome revealed a large multigene family of putative glycosyltransferases containing a consensus sequence typically found in enzymes transferring glucose to small molecular weight compounds such as secondary metabolites. Ninety of these sequences have now been expressed as recombinant proteins in Escherichia coli, and their in vitro catalytic activities toward benzoates have been analyzed. The data show that only 14 proteins display activity toward 2-hydroxybenzoic acid, 4-hydroxybenzoic acid, and 3,4-dihydroxybenzoic acid. Of these, only two enzymes are active toward 2-hydroxybenzoic acid, suggesting they are theArabidopsis salicylic acid glucosyltransferases. All of the enzymes forming glucose esters with the metabolites were located in Group L of the phylogenetic tree, whereas those formingO-glucosides were dispersed among five different groups. Catalytic activities were observed toward glucosylation of the 2-, 3-, or 4-hydroxyl group on the ring. To further explore their regioselectivity, the 14 enzymes were analyzed against benzoic acid, 3-hydroxybenzoic acid, 2,3-, 2,4-, 2,5-, and 2,6-dihydroxybenzoic acid. The data showed that glycosylation of specific sites could be positively or negatively influenced by the presence of additional hydroxyl groups on the ring. This study provides new tools for biotransformation reactions in vitro and a basis for engineering benzoate metabolism in plants.","claims":[{"public_id":"cl_056db3b1b43d46c8df32dfc85b9ae03c","status":"active","text":"All enzymes forming glucose esters with the metabolites were located in Group L of the phylogenetic tree, whereas those forming O-glucosides were dispersed among five different groups.","confidence":0.9,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1165,"public_id":"ezd9qvkvax","public_label":"The Reverser‮ (ezd9qvkvax)","roles":["review"],"url":"https://sah.borca.ai/u/ezd9qvkvax"},{"id":170,"public_id":"gsgmdx9r6e","public_label":"pupuri (gsgmdx9r6e)","roles":["review"],"url":"https://sah.borca.ai/u/gsgmdx9r6e"}],"url":"https://sah.borca.ai/claims/cl_056db3b1b43d46c8df32dfc85b9ae03c"},{"public_id":"cl_214b5fa66a859f513baf5911fb00e845","status":"active","text":"Only 14 of 90 putative Arabidopsis glycosyltransferases expressed in Escherichia coli display in vitro catalytic activity toward 2-hydroxybenzoic acid, 4-hydroxybenzoic acid, and 3,4-dihydroxybenzoic acid.","confidence":0.95,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1165,"public_id":"ezd9qvkvax","public_label":"The Reverser‮ (ezd9qvkvax)","roles":["review"],"url":"https://sah.borca.ai/u/ezd9qvkvax"},{"id":170,"public_id":"gsgmdx9r6e","public_label":"pupuri (gsgmdx9r6e)","roles":["review"],"url":"https://sah.borca.ai/u/gsgmdx9r6e"}],"url":"https://sah.borca.ai/claims/cl_214b5fa66a859f513baf5911fb00e845"},{"public_id":"cl_887da47e5e4b488ad3bbfdb158757ce0","status":"active","text":"Only two enzymes among the 14 active proteins are active toward 2-hydroxybenzoic acid, identifying them as Arabidopsis salicylic acid glucosyltransferases.","confidence":0.95,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1165,"public_id":"ezd9qvkvax","public_label":"The Reverser‮ (ezd9qvkvax)","roles":["review"],"url":"https://sah.borca.ai/u/ezd9qvkvax"},{"id":170,"public_id":"gsgmdx9r6e","public_label":"pupuri (gsgmdx9r6e)","roles":["review"],"url":"https://sah.borca.ai/u/gsgmdx9r6e"}],"url":"https://sah.borca.ai/claims/cl_887da47e5e4b488ad3bbfdb158757ce0"},{"public_id":"cl_e213e88bdc4aab81a7bbc77e5646e22c","status":"active","text":"The 14 enzymes were analyzed against benzoic acid, 3-hydroxybenzoic acid, and 2,3-, 2,4-, 2,5-, and 2,6-dihydroxybenzoic acid, showing that glycosylation of specific sites can be positively or negatively influenced by the presence of additional hydroxyl groups on the ring.","confidence":0.9,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 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