KEGG   PATHWAY: ko00333
Entry
ko00333                     Pathway                                
Name
Prodigiosin biosynthesis
Description
Prodiginines are red-pigmented natural antibiotics that are produced as secondary metabolites and have received renewed attention because of potential clinical interests. In Serratia sp. or actinomycetes such as Streptomyces coelicolor, the tripyrrole molecules of prodigiosin and undecylprodigiosin are formed by the condensation of 4-methoxy-2,2'-bipyrrole-5-carbaldehyde and either 2-methyl-3-n-amyl-pyrrole [MD:M00837] or 2-undecylpyrrole [MD:M00838]. The Serratia pig gene cluster and the Streptomyces red gene cluster responsible for these biosynthesis pathways have been identified.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
ko00333  Prodigiosin biosynthesis
ko00333

Module
M00837  Prodigiosin biosynthesis, L-proline => prodigiosin [PATH:ko00333]
M00838  Undecylprodigiosin biosynthesis, L-proline => undecylprodigiosin [PATH:ko00333]
Orthology
K21428  3-acetyloctanal synthase [EC:2.2.1.12]
K21778  3-acetyloctanal aminotransferase [EC:2.6.1.-]
K21779  2-methyl-3-n-amyl-dihydropyrrolel dehydrogenase
K21780  L-proline---[L-prolyl-carrier protein] ligase [EC:6.2.1.53]
K21781  peptidyl carrier protein
K21782  L-prolyl-PCP dehydrogenase [EC:1.3.8.14]
K21783  beta-ketoacyl ACP synthase [EC:2.3.1.-]
K21784  4-hydroxy-2,2'-bipyrrole-5-methanol synthase
K21785  4-hydroxy-2,2'-bipyrrole-5-methanol dehydrogenase
K21786  4-hydroxy-2,2'-bipyrrole-5-carbaldehyde O-methyltransferase [EC:2.1.1.-]
K21787  prodigiosin/undecylprodigiosin synthetase
K00645  [acyl-carrier-protein] S-malonyltransferase [EC:2.3.1.39]
K21788  dodecanoy-ACP synthase
K00059  3-oxoacyl-[acyl-carrier protein] reductase [EC:1.1.1.100]
K00208  enoyl-[acyl-carrier protein] reductase I [EC:1.3.1.9 1.3.1.10]
K21789  dodecanoy-ACP synthase
K21790  acyl carrier protein
K21791  thioesterase
K21792  polyketide synthase
K21793  oxidoreductase
Compound
C00083  Malonyl-CoA
C00148  L-Proline
C02679  Dodecanoic acid
C05223  Dodecanoyl-[acyl-carrier protein]
C12023  Undecylprodigiosin
C12470  L-Prolyl-[pcp]
C12483  Pyrrole-2-carbonyl-[pcp]
C21138  trans-2-Octenal
C21139  (S)-3-Acetyloctanal
C21565  Prodigiosin
C21567  Pyrrolyl-2-carboxyl-S-[acyl-carrier protein]
C21568  4-Hydroxy-2,2'-bipyrrole-5-methanol
C21569  4-Hydroxy-2,2'-bipyrrole-5-carbaldehyde
C21570  4-Methoxy-2,2'-bipyrrole-5-carbaldehyde
C21571  2-Methyl-3-n-amyl-dihydropyrrole
C21572  2-Methyl-3-n-amyl-pyrrole
C21573  4-Keto-2-undecylpyrroline
C21574  2-Undecylpyrrole
Reference
  Authors
Williamson NR, Simonsen HT, Ahmed RA, Goldet G, Slater H, Woodley L, Leeper FJ, Salmond GP
  Title
Biosynthesis of the red antibiotic, prodigiosin, in Serratia: identification of a novel 2-methyl-3-n-amyl-pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces.
  Journal
Mol Microbiol 56:971-89 (2005)
DOI:10.1111/j.1365-2958.2005.04602.x
Reference
  Authors
Cerdeno AM, Bibb MJ, Challis GL
  Title
Analysis of the prodiginine biosynthesis gene cluster of Streptomyces coelicolor A3(2): new mechanisms for chain initiation and termination in modular multienzymes.
  Journal
Chem Biol 8:817-29 (2001)
DOI:10.1016/S1074-5521(01)00054-0
Reference
  Authors
Harris AK, Williamson NR, Slater H, Cox A, Abbasi S, Foulds I, Simonsen HT, Leeper FJ, Salmond GP
  Title
The Serratia gene cluster encoding biosynthesis of the red antibiotic, prodigiosin, shows species- and strain-dependent genome context variation.
  Journal
Microbiology 150:3547-60 (2004)
DOI:10.1099/mic.0.27222-0
Reference
  Authors
Williamson NR, Fineran PC, Leeper FJ, Salmond GP
  Title
The biosynthesis and regulation of bacterial prodiginines.
  Journal
Nat Rev Microbiol 4:887-99 (2006)
DOI:10.1038/nrmicro1531
Related
pathway
ko00330  Arginine and proline metabolism
ko00620  Pyruvate metabolism
LinkDB

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