KEGG   ORTHOLOGY: K12707
Entry
K12707                      KO                                     
Symbol
novQ, cloQ
Name
4-hydroxyphenylpyruvate 3-dimethylallyltransferase [EC:2.5.1.111]
Pathway
map00401  Novobiocin biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R06757  dimethylallyl diphosphate:4-hydroxyphenylpyruvate 3-dimethylallyltransferase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00401 Novobiocin biosynthesis
    K12707  novQ, cloQ; 4-hydroxyphenylpyruvate 3-dimethylallyltransferase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01006 Prenyltransferases
    K12707  novQ, cloQ; 4-hydroxyphenylpyruvate 3-dimethylallyltransferase
Enzymes [BR:ko01000]
 2. Transferases
  2.5  Transferring alkyl or aryl groups, other than methyl groups
   2.5.1  Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
    2.5.1.111  4-hydroxyphenylpyruvate 3-dimethylallyltransferase
     K12707  novQ, cloQ; 4-hydroxyphenylpyruvate 3-dimethylallyltransferase
Prenyltransferases [BR:ko01006]
 Compound prenylation
  ABBA prenyltransferase
   K12707  novQ, cloQ; 4-hydroxyphenylpyruvate 3-dimethylallyltransferase
Genes
NGV: CDO52_02230
AG: AAF67510(novQ) AAN65239(cloQ)
Reference
PMID:12777382
  Authors
Pojer F, Kahlich R, Kammerer B, Li SM, Heide L.
  Title
CloR, a bifunctional non-heme iron oxygenase involved in clorobiocin biosynthesis.
  Journal
J Biol Chem 278:30661-8 (2003)
DOI:10.1074/jbc.M303190200
LinkDB

KEGG   ENZYME: 2.5.1.111
Entry
EC 2.5.1.111                Enzyme                                 
Name
4-hydroxyphenylpyruvate 3-dimethylallyltransferase;
CloQ;
4HPP dimethylallyltransferase;
NovQ;
dimethylallyl diphosphate:4-hydroxyphenylpyruvate 3-dimethylallyltransferase
Class
Transferases;
Transferring alkyl or aryl groups, other than methyl groups;
Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
Sysname
prenyl-diphosphate:3-(4-hydroxyphenyl)pyruvate 3'-prenyltransferase
Reaction(IUBMB)
prenyl diphosphate + 3-(4-hydroxyphenyl)pyruvate = diphosphate + 3-(4-hydroxy-3-prenylphenyl)pyruvate [RN:R06757]
Reaction(KEGG)
R06757
Substrate
prenyl diphosphate [CPD:C00235];
3-(4-hydroxyphenyl)pyruvate [CPD:C01179]
Product
diphosphate [CPD:C00013];
3-(4-hydroxy-3-prenylphenyl)pyruvate [CPD:C12456]
Comment
The enzyme's product feeds into the biosynthesis of the aminocoumarin antibiotics clorobiocin and novobiocin [1].
History
EC 2.5.1.111 created 2013
Pathway
ec00401  Novobiocin biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K12707  4-hydroxyphenylpyruvate 3-dimethylallyltransferase
Genes
NGV: CDO52_02230
Reference
1  [PMID:12618544]
  Authors
Pojer F, Wemakor E, Kammerer B, Chen H, Walsh CT, Li SM, Heide L.
  Title
CloQ, a prenyltransferase involved in clorobiocin biosynthesis.
  Journal
Proc Natl Acad Sci U S A 100:2316-21 (2003)
DOI:10.1073/pnas.0337708100
  Sequence
[ag:AAN65239]
Reference
2  [PMID:17077503]
  Authors
Keller S, Pojer F, Heide L, Lawson DM
  Title
Crystallization and preliminary X-ray analysis of the aromatic prenyltransferase  CloQ from the clorobiocin biosynthetic cluster of Streptomyces roseochromogenes.
  Journal
Acta Crystallogr Sect F Struct Biol Cryst Commun 62:1153-5 (2006)
DOI:10.1107/S1744309106042527
Reference
3  [PMID:20946900]
  Authors
Metzger U, Keller S, Stevenson CE, Heide L, Lawson DM
  Title
Structure and mechanism of the magnesium-independent aromatic prenyltransferase CloQ from the clorobiocin biosynthetic pathway.
  Journal
J Mol Biol 404:611-26 (2010)
DOI:10.1016/j.jmb.2010.09.067
  Sequence
[ag:AAN65239]
Reference
4  [PMID:19557032]
  Authors
Ozaki T, Mishima S, Nishiyama M, Kuzuyama T
  Title
NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids.
  Journal
J Antibiot (Tokyo) 62:385-92 (2009)
DOI:10.1038/ja.2009.48
  Sequence
[ag:AAF67510]
Other DBs
ExplorEnz - The Enzyme Database: 2.5.1.111
IUBMB Enzyme Nomenclature: 2.5.1.111
ExPASy - ENZYME nomenclature database: 2.5.1.111
BRENDA, the Enzyme Database: 2.5.1.111
LinkDB

KEGG   REACTION: R06757
Entry
R06757                      Reaction                               
Name
dimethylallyl diphosphate:4-hydroxyphenylpyruvate 3-dimethylallyltransferase
Definition
3-(4-Hydroxyphenyl)pyruvate + Dimethylallyl diphosphate <=> 3-Dimethylallyl-4-hydroxyphenylpyruvate + Diphosphate
Equation
C01179 + C00235 <=> C12456 + C00013
Comment
prenyltransferase, NovQ CloQ
Reaction class
RC00209  C01179_C12456
Enzyme
2.5.1.111
Pathway
rn00401  Novobiocin biosynthesis
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 2. Transferase reactions
  2.5  Transferring alkyl or aryl groups, other than methyl groups
   2.5.1  Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
    2.5.1.111
     R06757  3-(4-Hydroxyphenyl)pyruvate + Dimethylallyl diphosphate <=> 3-Dimethylallyl-4-hydroxyphenylpyruvate + Diphosphate
Orthology
K12707  4-hydroxyphenylpyruvate 3-dimethylallyltransferase [EC:2.5.1.111]
Other DBs
RHEA: 37058
LinkDB

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