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Results 1 - 9 of 9
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EC Number Substrates Commentary Substrates Organism Products Commentary (Products) Reversibility
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.2222 2,3-dimethyl-4(1H)-quinolinone + NAD(P)H + H+ + O2 methyl variant of aurachin D Stigmatella aurantiaca 3-hydroxy-2-[(3-hydroxy-3-methyl-4-oxo-1,2,3,4-tetrahydroquinolin-2-yl)methyl]-3-methylquinolin-4(3H)-one + NAD(P)+ + H2O product is formed by dimerization ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.2222-methyl-3-geranyl-4(1H)-quinolinone + NAD(P)H + H+ + O2 geranyl variant of aurachin D Stigmatella aurantiaca 3-[(3,7-dimethylocta-1,6-dien-3-yl)oxy]-2-methyl-2,3-dihydroquinolin-4(1H)-one + NAD(P)+ + H2O - ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.2222-methyl-3-isoprenyl-4(1H)-quinolinone + NAD(P)H + H+ + O2 isoprenyl variant of aurachin D Stigmatella aurantiaca 2-methyl-3-[(2-methylbut-3-en-2-yl)oxy]-2,3-dihydroquinolin-4(1H)-one + NAD(P)+ + H2O during the AuaG-catalysed transformation, the transient C2-C3 epoxide can be formed and opened to the tertiary alcoholate. The ether product is supposed to arise from rapid retro-[2,3]-Wittig rearrangement assisted by the presence of both carbonyl and iminium functions ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.222aurachin C + NAD(P)H + H+ + O2 - Stigmatella aurantiaca 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD(P)+ + H2O AuaG performs epoxidation of the C2-C3 bond of aurachin C. The resulting epoxide is opened, thereby resulting in the imine N-oxide and the alpha-keto tertiary alcoholate ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.222aurachin C + NAD(P)H + H+ + O2 - Stigmatella aurantiaca 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD(P)+ + H2O overall reaction, the product of AuaG is highly unstable and rapidly isomerizes in 0.1 M CHES (pH 9.5)/methanol ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.222aurachin C + NADH + H+ + O2 - Stigmatella aurantiaca 4-hydroxy-2-methyl-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]quinolin-3(4H)-one 1-oxide + NAD+ + H2O formation of aurachin B requires the presence of AuaH. AuaG and AuaH act sequentially and conversion of aurachin C into aurachin B occurs by oxidation and subsequent reduction ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.222aurachin C + NADH + O2 - Stigmatella aurantiaca 4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide + NAD+ + H2O - ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.222aurachin C + NADH + O2 first step in the conversion of aurachin C to aurachin. The FAD-dependent monooxygenase catalyses the epoxidation of the C2-C3 double bond of aurachin C, this is followed by a semipinacol rearrangement, causing migration of the farnesyl group from C3 to C4 Stigmatella aurantiaca 4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide + NAD+ + H2O - ?
Display the word mapDisplay the reaction diagram Show all sequences 1.14.13.222more AuaG is able to oxidize short-chain analogues of aurachin D. A retro-[2,3]-Wittig rearrangement is observed with isoprenyl substrate analogues. Saturated-chain analogues of N-oxidized aurachin C are not transformed by the C3 to C4 semipinacol reaction Stigmatella aurantiaca ? - ?
Results 1 - 9 of 9
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