KEGG   PATHWAY: ko00401
Entry
ko00401                     Pathway                                
Name
Novobiocin biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
ko00401  Novobiocin biosynthesis
ko00401

Drug
D02333  Coumermycin (USAN)
Other DBs
GO: 0043642
Orthology
K00220  tyrC; cyclohexadieny/prephenate dehydrogenase [EC:1.3.1.43 1.3.1.12]
K00812  aspB; aspartate aminotransferase [EC:2.6.1.1]
K00813  aspC; aspartate aminotransferase [EC:2.6.1.1]
K00815  TAT; tyrosine aminotransferase [EC:2.6.1.5]
K00817  hisC; histidinol-phosphate aminotransferase [EC:2.6.1.9]
K00832  tyrB; aromatic-amino-acid transaminase [EC:2.6.1.57]
K00838  ARO8; aromatic amino acid aminotransferase I / 2-aminoadipate transaminase [EC:2.6.1.57 2.6.1.39 2.6.1.27 2.6.1.5]
K04517  tyrA2; prephenate dehydrogenase [EC:1.3.1.12]
K11358  yhdR; aspartate aminotransferase [EC:2.6.1.1]
K12701  novH; novobiocin biosynthesis protein NovH
K12702  novI, CYP163A; novobiocin biosynthesis protein NovI
K12703  novJ; novobiocin biosynthesis protein NovJ
K12704  novK; novobiocin biosynthesis protein NovK
K12705  novO, couO; 8-demethylnovobiocic acid C8-methyltransferase [EC:2.1.1.284]
K12707  novQ, cloQ; 4-hydroxyphenylpyruvate 3-dimethylallyltransferase [EC:2.5.1.111]
K12708  novR, cloR; 4-hydroxy-3-prenylphenylpyruvate oxygenase / 4-hydroxy-3-prenylbenzoate synthase [EC:1.13.11.83 1.13.12.23]
K12709  novL, cloL, couL; 8-demethylnovobiocic acid synthase [EC:6.3.1.15]
K12711  novM, cloM, couM; L-demethylnoviosyl transferase [EC:2.4.1.302]
K12712  novP, cloP, couP; demethyldecarbamoylnovobiocin O-methyltransferase [EC:2.1.1.285]
K12713  novN; decarbamoylnovobiocin carbamoyltransferase [EC:2.1.3.12]
K12714  clohal; clorobiocin biosynthesis protein Clo-hal
K12719  cloN4, couN4; L-proline---[L-prolyl-carrier protein] ligase [EC:6.2.1.53]
K12720  cloN5, couN5; peptidyl carrier protein
K12721  cloN3, couN3; L-prolyl-[peptidyl-carrier protein] dehydrogenase [EC:1.3.8.14]
K12722  cloN6, couN6; clorobiocin/coumermycin A biosynthesis protein CloN6/CouN6
K12723  cloN2; clorobiocin biosynthesis protein CloN2
K12724  cloN7, couN7; clorobiocin/coumermycin A biosynthesis protein CloN7/CouN7
K14187  tyrA; chorismate mutase / prephenate dehydrogenase [EC:5.4.99.5 1.3.1.12]
K17626  cloN1; clorobiocin biosynthesis protein CloN1
K24018  K24018; cyclohexadieny/prephenate dehydrogenase / 3-phosphoshikimate 1-carboxyvinyltransferase
Compound
C00082  L-Tyrosine
C00148  L-Proline
C00254  Prephenate
C01179  3-(4-Hydroxyphenyl)pyruvate
C05073  Coumermycin A1
C05080  Novobiocin
C12032  Clorobiocin
C12456  3-Dimethylallyl-4-hydroxyphenylpyruvate
C12457  3-Dimethylallyl-4-hydroxymandelic acid
C12458  3-Dimethylallyl-4-hydroxybenzoate
C12459  3-Dimethylallyl-4-hydroxybenzaldehyde
C12460  3-Dimethylallyl-beta-hydroxy-L-tyrosyl-[pcp]
C12461  L-Tyrosyl-[pcp]
C12462  beta-Hydroxy-L-tyrosyl-[pcp]
C12463  beta-Keto-L-tyrosyl-[pcp]
C12467  2-Hydroxy-beta-keto-L-tyrosyl-[pcp]
C12468  3-Amino-4,7-dihydroxycoumarin
C12469  3-Amino-4,7-dihydroxy-8-chlorocoumarin
C12470  L-Prolyl-[pcp]
C12471  Chlorobiocic acid
C12472  Novclobiocin 105
C12473  Novclobiocin 104
C12474  Novobiocic acid
C12475  Demethyldecarbamoylnovobiocin
C12476  Decarbamoylnovobiocin
C12477  3-Methylpyrrole-2,4-dicarboxylic acid
C12479  Coumermic acid
C12480  Coumermycin D
C12481  dTDP-5-dimethyl-L-lyxose
C12483  Pyrrole-2-carbonyl-[pcp]
C20629  8-Demethylnovobiocic acid
C20637  5-[[(4,7-Dihydroxy-2-oxo-2H-1-benzopyran-3-yl)amino]carbonyl]-4-methyl-1H-pyrrole-3-carboxylate
Reference
PMID:12480894
  Authors
Pojer F, Li SM, Heide L.
  Title
Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics.
  Journal
Microbiology 148:3901-11 (2002)
DOI:10.1099/00221287-148-12-3901
Reference
PMID:11325587
  Authors
Chen H, Walsh CT.
  Title
Coumarin formation in novobiocin biosynthesis: beta-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI.
  Journal
Chem Biol 8:301-12 (2001)
DOI:10.1016/S1074-5521(01)00009-6
Reference
PMID:14622269
  Authors
Schmutz E, Steffensky M, Schmidt J, Porzel A, Li SM, Heide L.
  Title
An unusual amide synthetase (CouL) from the coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis DSM 40489.
  Journal
Eur J Biochem 270:4413-9 (2003)
DOI:10.1046/j.1432-1033.2003.03830.x
Reference
PMID:12904558
  Authors
Xu H, Kahlich R, Kammerer B, Heide L, Li SM.
  Title
CloN2, a novel acyltransferase involved in the attachment of the pyrrole-2-carboxyl moiety to the deoxysugar of clorobiocin.
  Journal
Microbiology 149:2183-91 (2003)
DOI:10.1099/mic.0.26314-0
Reference
PMID:12436260
  Authors
Xu H, Wang ZX, Schmidt J, Heide L, Li SM.
  Title
Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin.
  Journal
Mol Genet Genomics 268:387-96 (2002)
DOI:10.1007/s00438-002-0759-1
Reference
PMID:14694473
  Authors
Freel Meyers CL, Oberthur M, Xu H, Heide L, Kahne D, Walsh CT
  Title
Characterization of NovP and NovN: completion of novobiocin biosynthesis by sequential tailoring of the noviosyl ring.
  Journal
Angew Chem Int Ed Engl 43:67-70 (2004)
DOI:10.1002/anie.200352626
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
Reference
PMID:12368465
  Authors
Li SM, Westrich L, Schmidt J, Kuhnt C, Heide L.
  Title
Methyltransferase genes in Streptomyces rishiriensis: new coumermycin derivatives from gene-inactivation experiments.
  Journal
Microbiology 148:3317-26 (2002)
DOI:10.1099/00221287-148-10-3317
Reference
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
Related
pathway
ko00330  Arginine and proline metabolism
ko00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ko00523  Polyketide sugar unit biosynthesis

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