KEGG   ORTHOLOGY: K21272Help
Entry
K21272                      KO                                     

Name
auaG
Definition
aurachin C monooxygenase/isomerase [EC:1.14.13.222]
Pathway
ko00998  Biosynthesis of various secondary metabolites - part 2
ko01100  Metabolic pathways
ko01130  Biosynthesis of antibiotics
Module
M00848  Aurachin biosynthesis, anthranilate => aurachin A
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00998 Biosynthesis of various secondary metabolites - part 2
    K21272  auaG; aurachin C monooxygenase/isomerase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.222  aurachin C monooxygenase/isomerase
     K21272  auaG; aurachin C monooxygenase/isomerase
BRITE hierarchy
Other DBs
RN: R11382 R11383
COG: COG0654
GO: 0102563
Genes
MXA: MXAN_3398
MFU: LILAB_24765
MYM: A176_003540
CCX: COCOR_04724
AG: CCD27744(auaG)
TaxonomyKoalaUniProt
Reference
  Authors
Katsuyama Y, Harmrolfs K, Pistorius D, Li Y, Muller R
  Title
A semipinacol rearrangement directed by an enzymatic system featuring dual-function FAD-dependent monooxygenase.
  Journal
Angew Chem Int Ed Engl 51:9437-40 (2012)
DOI:10.1002/anie.201204138
  Sequence

KEGG   ENZYME: 1.14.13.222Help
Entry
EC 1.14.13.222              Enzyme                                 

Name
aurachin C monooxygenase/isomerase;
auaG (gene name);
aurachin C monooxygenase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
aurachin C:NAD(P)H:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
Reaction(IUBMB)
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) [RN:R11382 R11383];
(1a) aurachin C + NAD(P)H + H+ + O2 = 2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one + NAD(P)+ + H2O [RN:R11384 R11385];
(1b) 2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one = 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide [RN:R11386]
Reaction(KEGG)
Substrate
aurachin C [CPD:C21330];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one [CPD:C21331]
Product
4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide [CPD:C21141];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one [CPD:C21331]
Comment
The aurachin C monooxygenase from the bacterium Stigmatella aurantiaca accepts both NADH and NADPH as cofactor, but has a preference for NADH. It catalyses the initial steps in the conversion of aurachin C to aurachin B. The FAD-dependent monooxygenase catalyses the epoxidation of the C2-C3 double bond of aurachin C, which is followed by a semipinacol rearrangement, causing migration of the farnesyl group from C3 to C4.
History
EC 1.14.13.222 created 2016
Pathway
ec00998  Biosynthesis of various secondary metabolites - part 2
ec01100  Metabolic pathways
ec01130  Biosynthesis of antibiotics
Orthology
K21272  aurachin C monooxygenase/isomerase
Genes
MXA: MXAN_3398
MFU: LILAB_24765
MYM: A176_003540
CCX: COCOR_04724
Taxonomy
Reference
1  [PMID:22907798]
  Authors
Katsuyama Y, Harmrolfs K, Pistorius D, Li Y, Muller R
  Title
A semipinacol rearrangement directed by an enzymatic system featuring dual-function FAD-dependent monooxygenase.
  Journal
Angew Chem Int Ed Engl 51:9437-40 (2012)
DOI:10.1002/anie.201204138
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.222
IUBMB Enzyme Nomenclature: 1.14.13.222
ExPASy - ENZYME nomenclature database: 1.14.13.222
BRENDA, the Enzyme Database: 1.14.13.222

KEGG   REACTION: R11382Help
Entry
R11382                      Reaction                               

Name
aurachin C:NADH:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
Definition
Aurachin C + NADH + H+ + Oxygen <=> 4-Hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD+ + H2O
Equation
Comment
two-step reaction (see R11384+R11386)
Reaction class
RC03422  C21141_C21330
Enzyme
Pathway
rn00998  Biosynthesis of various secondary metabolites - part 2
rn01100  Metabolic pathways
rn01130  Biosynthesis of antibiotics
Module
M00848  Aurachin biosynthesis, anthranilate => aurachin A
Orthology
K21272  aurachin C monooxygenase/isomerase [EC:1.14.13.222]
Other DBs
RHEA: 49003

KEGG   REACTION: R11383Help
Entry
R11383                      Reaction                               

Name
aurachin C:NADPH:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
Definition
Aurachin C + NADPH + H+ + Oxygen <=> 4-Hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NADP+ + H2O
Equation
Comment
two-step reaction (see R11385+R11386)
Reaction class
RC03422  C21141_C21330
Enzyme
Pathway
rn00998  Biosynthesis of various secondary metabolites - part 2
rn01100  Metabolic pathways
rn01130  Biosynthesis of antibiotics
Module
M00848  Aurachin biosynthesis, anthranilate => aurachin A
Orthology
K21272  aurachin C monooxygenase/isomerase [EC:1.14.13.222]
Other DBs
RHEA: 49007

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