Literature summary for 1.14.13.222 extracted from

Katsuyama, Y.; Harmrolfs, K.; Pistorius, D.; Li, Y. and Muller, R.
A semipinacol rearrangement directed by an enzymatic system featuring dual-function FAD-dependent monooxygenase (2012), Angew. Chem. Int. Ed. Engl., 51, 9437-9440.

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Cloned(Commentary)

Cloned (Comment)	Organism
expressed in Escherichia coli	Stigmatella aurantiaca
expression in Escherichia coli	Stigmatella aurantiaca

Molecular Weight [Da]

Molecular Weight [Da]	Molecular Weight Maximum [Da]	Comment	Organism
41290	-	calculated from amino acid sequence	Stigmatella aurantiaca

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
aurachin C + NADH + O2	Stigmatella aurantiaca	-	4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide + NAD+ + H2O	-	?

Organism

Organism	UniProt	Comment	Textmining
Stigmatella aurantiaca	H1ZZA4	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
aurachin 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	?
aurachin 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	?
aurachin C + NADH + O2	-	Stigmatella aurantiaca	4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide + NAD+ + H2O	-	?
aurachin 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	-	?

Synonyms

Synonyms	Comment	Organism
auaG	-	Stigmatella aurantiaca

Cofactor

Cofactor	Comment	Organism	Structure
FAD	contains an FAD binding domain	Stigmatella aurantiaca
FAD	AuaG purifies as a slightly yellow protein and the binding cofactor is flavinadenine dinucleotide	Stigmatella aurantiaca
NADH	NADH is preferred over NADPH	Stigmatella aurantiaca
NADH	preferred over NADPH	Stigmatella aurantiaca
NADPH	NADH is preferred over NADPH	Stigmatella aurantiaca

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Release 2023.1 (January 2023)