KEGG   ORTHOLOGY: K21271
Entry
K21271            Tight     KO                                     

Name
auaH
Definition
aurachin B dehydrogenase [EC:1.1.1.394]
Pathway
ko00998  Biosynthesis of various secondary metabolites - part 2
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
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
    K21271  auaH; aurachin B dehydrogenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.394  aurachin B dehydrogenase
     K21271  auaH; aurachin B dehydrogenase
Other DBs
RN: R11149
COG: COG0451
Genes
AG: CCD27750(auaH)
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: 1.1.1.394
Entry
EC 1.1.1.394                Enzyme                                 

Name
aurachin B dehydrogenase;
AuaH
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
aurachin B:NAD+ 3-oxidoreductase
Reaction(IUBMB)
aurachin B + NAD+ + H2O = 4-[(2E,6E)-farnesyl]-4-hydroxy-2-methyl-3-oxo-3,4-dihydroquinoline 1-oxide + NADH + H+ (overall reaction) [RN:R11149];
(1a) 4-[(2E,6E)-farnesyl]-3,4-dihydroxy-2-methyl-3,4-dihydroquinoline 1-oxide + NAD+ = 4-[(2E,6E)-farnesyl]-4-hydroxy-2-methyl-3-oxo-3,4-dihydroquinoline 1-oxide + NADH + H+ [RN:R11147];
(1b) aurachin B + H2O = 4-[(2E,6E)-farnesyl]-3,4-dihydroxy-2-methyl-3,4-dihydroquinoline 1-oxide (spontaneous) [RN:R11148]
Reaction(KEGG)
Substrate
aurachin B [CPD:C21140];
NAD+ [CPD:C00003];
H2O [CPD:C00001];
4-[(2E,6E)-farnesyl]-3,4-dihydroxy-2-methyl-3,4-dihydroquinoline 1-oxide
Product
4-[(2E,6E)-farnesyl]-4-hydroxy-2-methyl-3-oxo-3,4-dihydroquinoline 1-oxide;
NADH [CPD:C00004];
H+ [CPD:C00080];
4-[(2E,6E)-farnesyl]-3,4-dihydroxy-2-methyl-3,4-dihydroquinoline 1-oxide (spontaneous)
Comment
The enzyme from the bacterium Stigmatella aurantiaca catalyses the final step in the conversion of aurachin C to aurachin B. In vivo the enzyme catalyses the reduction of 4-[(2E,6E)-farnesyl]-4-hydroxy-2-methyl-3-oxo-3,4-dihydroquinoline-1-oxide to form 4-[(2E,6E)-farnesyl]-2-methyl-1-oxo-3,4-dihydroquinoline-3,4-diol (note that the reactions written above proceed from right to left), which then undergoes a spontaneous dehydration to form aurachin B.
History
EC 1.1.1.394 created 2016
Pathway
ec00998  Biosynthesis of various secondary metabolites - part 2
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K21271  aurachin B dehydrogenase
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: 1.1.1.394
IUBMB Enzyme Nomenclature: 1.1.1.394
ExPASy - ENZYME nomenclature database: 1.1.1.394
BRENDA, the Enzyme Database: 1.1.1.394

KEGG   REACTION: R11149
Entry
R11149                      Reaction                               

Name
aurachin B:NAD+ 3-oxidoreductase
Definition
Aurachin B + NAD+ + H2O <=> 4-Hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NADH + H+
Equation
Comment
two-step reaction (see R11148+R11147)
Reaction class
RC00001  C00003_C00004
RC03371  C21140_C21141
Enzyme
Pathway
rn00998  Biosynthesis of various secondary metabolites - part 2
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00848  Aurachin biosynthesis, anthranilate => aurachin A
Orthology
K21271  aurachin B dehydrogenase [EC:1.1.1.394]

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