KEGG   PATHWAY: rn00333
Entry
rn00333                     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
rn00333  Prodigiosin biosynthesis
rn00333

Module
M00837  Prodigiosin biosynthesis, L-proline => prodigiosin [PATH:rn00333]
M00838  Undecylprodigiosin biosynthesis, L-proline => undecylprodigiosin [PATH:rn00333]
Reaction
R04014  dodecanoyl-[acyl-carrier-protein] hydrolase
R06746  L-proline:[peptidyl-carrier protein] ligase (AMP-forming)
R06747  L-prolyl-[peptidyl-carrier protein]:electron-transfer flavoprotein oxidoreductase
R11141  pyruvate:(E)-oct-2-enal acetaldehydetransferase (decarboxylating)
R11661  2-methyl-3-n-amyl-dihydropyrrole:amine oxidoreductase
R11662   
R11663  4-keto-2-undecylpyrroline, NADPH: oxidoreductase
R11664   
R11665   
R11666  4-keto-2-undecylpyrroline, NADH: oxidoreductase
R11667   
R11668  4-hydroxy-2,2'-bipyrrole-5-methanal:NADP+ oxidoreductase
R11669  4-hydroxy-2,2'-bipyrrole-5-methanal:NAD+ oxidoreductase
R11670  S-adenosyl-L-methionine:4-Hydroxy-2,2'-bipyrrole-5-carbaldehyde 4-O-methyltransferase
R11671   
R11672   
R11673   
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
rn00330  Arginine and proline metabolism
rn00620  Pyruvate metabolism
KO pathway
ko00333   

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