1.14.13.222: aurachin C monooxygenase/isomerase
This is an abbreviated version!
For detailed information about aurachin C monooxygenase/isomerase, go to the full flat file.
Word Map on EC 1.14.13.222
-
1.14.13.222
-
binuclear
-
actinomycete
-
smegmatis
-
mycobacteria
-
phenol
-
propane
-
chaperonin
- 1.14.13.222
-
binuclear
-
actinomycete
- smegmatis
- mycobacteria
- phenol
- propane
- chaperonin
Reaction
Synonyms
auaG, aurachin C monooxygenase, MimA, MimABCD, Msmeg_1971
ECTree
1.14.13.222 aurachin C monooxygenase/isomeraseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.14.13.222 - aurachin C monooxygenase/isomerase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 2,3-dimethyl-4(1H)-quinolinone + NAD(P)H + H+ + O2
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
methyl variant of aurachin D
product is formed by dimerization
-
?
2-methyl-3-geranyl-4(1H)-quinolinone + NAD(P)H + H+ + O2
3-[(3,7-dimethylocta-1,6-dien-3-yl)oxy]-2-methyl-2,3-dihydroquinolin-4(1H)-one + NAD(P)+ + H2O
geranyl variant of aurachin D
-
-
?
2-methyl-3-isoprenyl-4(1H)-quinolinone + NAD(P)H + H+ + O2
2-methyl-3-[(2-methylbut-3-en-2-yl)oxy]-2,3-dihydroquinolin-4(1H)-one + NAD(P)+ + H2O
isoprenyl variant of aurachin D
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
-
?
aurachin C + NAD(P)H + H+ + O2
4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD(P)+ + H2O
aurachin C + NADH + H+ + O2
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
-
?
aurachin C + NADH + O2
4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide + NAD+ + H2O
additional information
?
-
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
-
-
?
aurachin C + NAD(P)H + H+ + O2
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
-
?
aurachin C + NAD(P)H + H+ + O2
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
-
?
aurachin C + NADH + O2
4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide + NAD+ + H2O
-
-
-
?
aurachin C + NADH + O2
4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide + NAD+ + H2O
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
-
-
?
