KEGG   PATHWAY: sco00333
Entry
sco00333                    Pathway                                
Name
Prodigiosin biosynthesis - Streptomyces coelicolor
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
sco00333  Prodigiosin biosynthesis
sco00333

Organism
Streptomyces coelicolor [GN:sco]
Gene
SCO0330  fabG; 3-ketoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
SCO1346  2SCG61.28c; 3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
SCO1815  fabG; 3-oxacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
SCO1831  SCI8.16; oxidoreductase [KO:K00059] [EC:1.1.1.100]
SCO2387  fabD; ACP S-malonyltransferase [KO:K00645] [EC:2.3.1.39]
SCO3502  SCE134.03c; 3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
SCO4501  fabG; 3-ketoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
SCO4681  SCD31.06; short chain dehydrogenase [KO:K00059] [EC:1.1.1.100]
SCO5878  redX; polyketide synthase RedX [KO:K21783] [EC:2.3.1.-]
SCO5879  redW; acyl-coa dehydrogenase RedW [KO:K21782] [EC:1.3.8.14]
SCO5882  redV; RedV protein [KO:K21785]
SCO5886  redR; 3-oxoacyl-ACP synthase [KO:K21789]
SCO5887  redQ; acyl carrier protein [KO:K21790]
SCO5888  redP; 3-oxoacyl-ACP synthase III [KO:K21788]
SCO5889  redO; hypothetical protein [KO:K21781]
SCO5890  redN; 8-amino-7-oxononanoate synthase [KO:K21784]
SCO5891  redM; peptide synthase [KO:K21780] [EC:6.2.1.53]
SCO5892  redL; polyketide synthase [KO:K21792]
SCO5893  redK; oxidoreductase [KO:K21793]
SCO5894  redJ; thioesterase [KO:K21791]
SCO5895  redI; methyltransferase [KO:K27675]
SCO5896  redH; phosphoenolpyruvate-utilizing enzyme [KO:K21787]
SCO6249  SCAH10.14c; 3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
SCO6264  SCAH10.29; reductase [KO:K00059] [EC:1.1.1.100]
SCO7266  SC5H1.26; 3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
SCO7810  SC8E7.07; oxidoreductase [KO:K00059] [EC:1.1.1.100]
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
sco00330  Arginine and proline metabolism
sco00620  Pyruvate metabolism
KO pathway
ko00333   

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