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Bacterial Aryl Sulfotransferases in Selective and Sustainable Sulfation of Biologically Active Compounds using Novel Sulfate Donors
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SYSNO ASEP 0561642 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Bacterial Aryl Sulfotransferases in Selective and Sustainable Sulfation of Biologically Active Compounds using Novel Sulfate Donors Author(s) Brodsky, Katerina (MBU-M) ORCID
Káňová, Kristýna (MBU-M) ORCID
Konvalinková, Dorota (MBU-M)
Slámová, Kristýna (MBU-M) RID, ORCID
Pelantová, Helena (MBU-M) ORCID, RID
Valentová, Kateřina (MBU-M) RID, ORCID
Bojarová, Pavla (MBU-M) ORCID
Křen, Vladimír (MBU-M) RID, ORCID
Petrásková, Lucie (MBU-M) ORCIDArticle number e202201253 Source Title ChemSusChem. - : Wiley - ISSN 1864-5631
Roč. 15, č. 18 (2022)Number of pages 9 s. Language eng - English Country DE - Germany Keywords aryl sulfotransferase ; biocatalysis ; enzyme catalysis ; leaving group ; sulfation Subject RIV CE - Biochemistry OECD category Biochemistry and molecular biology R&D Projects GA19-00043S GA ČR - Czech Science Foundation (CSF) Method of publishing Limited access Institutional support MBU-M - RVO:61388971 UT WOS 000831332600001 EID SCOPUS 85135030849 DOI 10.1002/cssc.202201253 Annotation Regioselective sulfation of bioactive compounds is a vital and scarcely studied topic in enzyme-catalyzed transformations and metabolomics. The major bottleneck of enzymatic sulfation consists in finding suitable sulfate donors. In this regard, 3 '-phosphoadenosine 5 '-phosphosulfate (PAPS)-independent aryl sulfotransferases using aromatic sulfate donors are a favored choice due to their cost-effectiveness. This work presents a unique study of five sulfate donors differing in their leaving group pK(a) values with a new His-tagged construct of aryl sulfotransferase from Desulfitobacterium hafniense (DhAST-tag). DhAST-tag was purified to homogeneity and biochemically characterized. Two new donors (3-nitrophenyl sulfate and 2-nitrophenyl sulfate) were synthesized. The kinetic parameters of these and other commercial sulfates (4-nitrophenyl, 4-methylumbelliferyl, and phenyl) revealed large differences with respect to the structure of the leaving group. These donors were screened for the sulfation of selected flavonoids (myricetin, chrysin) and phenolic acids (gallate, 3,4-dihydroxyphenylacetate). The donor impact on the sulfation regioselectivity and yield was assessed. The obtained regioselectively sulfated compounds are authentic human metabolites required as standards in clinical trials. Workplace Institute of Microbiology Contact Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Year of Publishing 2023 Electronic address https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.202201253
Number of the records: 1