About: Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver

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About: Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Aryl sulfotransferase IV (AstIV) from rat liver was overexpressed in Escherichia coli and purified to homogeneity. Using the produced mammalian liver enzyme, sulfation-the Phase II conjugation reaction-of optically pure silybin diastereoisomers (silybin A and B) was tested. As a result, silybin B was sulfated yielding 20-O-silybin B sulfate, whereas silybin A was completely resistant to the sulfation reaction. Milligram-scale sulfation of silybin B was optimized employing resting E. coli cells producing AstIV, thus avoiding the use of expensive 3'-phosphoadenosine-5'-phosphate cofactor and laborious enzyme purification. Using this approach, we were able to reach 48 % conversion of silybin B into its 20-sulfate within 24 h. The sulfated product was isolated by solid phase extraction and its structure was characterized by HRMS and NMR. Sulfation reaction of silybin appeared strictly stereoselective; only silybin B was sulfated by AstIV Aryl sulfotransferase IV (AstIV) from rat liver was overexpressed in Escherichia coli and purified to homogeneity. Using the produced mammalian liver enzyme, sulfation-the Phase II conjugation reaction-of optically pure silybin diastereoisomers (silybin A and B) was tested. As a result, silybin B was sulfated yielding 20-O-silybin B sulfate, whereas silybin A was completely resistant to the sulfation reaction. Milligram-scale sulfation of silybin B was optimized employing resting E. coli cells producing AstIV, thus avoiding the use of expensive 3'-phosphoadenosine-5'-phosphate cofactor and laborious enzyme purification. Using this approach, we were able to reach 48 % conversion of silybin B into its 20-sulfate within 24 h. The sulfated product was isolated by solid phase extraction and its structure was characterized by HRMS and NMR. Sulfation reaction of silybin appeared strictly stereoselective; only silybin B was sulfated by AstIV (en)
Title	Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver (en)
skos:prefLabel	Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver (en)
skos:notation	RIV/61388971:_____/13:00421796!RIV14-MSM-61388971
http://linked.open...avai/predkladatel	Mikrobiologický ústav AV ČR, v.v.i.
http://linked.open...avai/riv/aktivita	I P S
http://linked.open...avai/riv/aktivity	I, P(GAP301/11/0767), P(LD13042), S
http://linked.open...iv/cisloPeriodika	24
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Kuzma, Marek Slámová, Kristýna Křen, Vladimír Šulc, Miroslav Marhol, Petr Purchartová, Kateřina
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Mikrobiologický ústav AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	73077
http://linked.open...ai/riv/idVysledku	RIV/61388971:_____/13:00421796
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Silybin; Biotransformation; Diastereoisomers (en)
http://linked.open.../riv/klicoveSlovo	Diastereoisomers Silybin Biotransformation
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[7EBCC5971035]
http://linked.open...i/riv/nazevZdroje	Applied Microbiology and Biotechnology
http://linked.open...in/vavai/riv/obor	CE
http://linked.open...ichTvurcuVysledku	6 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	Enzymatic synthesis of multivalent glycoconjugates of natural and biologically active compounds. Modulation of intestinal inflammation and nitric oxide production by quercetin and its conjugates
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	97
http://linked.open...iv/tvurceVysledku	Elling, L. Křen, Vladimír Kuzma, Marek Slámová, Kristýna Šulc, Miroslav Marhol, Petr Purchartová, Kateřina Engels, L.
http://linked.open...ain/vavai/riv/wos	000327495000014
issn	0175-7598
number of pages	8 (xsd:int)
http://bibframe.org/vocab/doi	10.1007/s00253-013-4794-0

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