KEGG   PATHWAY: sgm00333
Entry
sgm00333                    Pathway                                
Name
Prodigiosin biosynthesis - Streptomyces aurantiacus
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
sgm00333  Prodigiosin biosynthesis
sgm00333

Module
sgm_M00838  Undecylprodigiosin biosynthesis, L-proline => undecylprodigiosin [PATH:sgm00333]
Organism
Streptomyces aurantiacus [GN:sgm]
Gene
GCM10017557_78140  D-alanine--poly(phosphoribitol) ligase [KO:K21780] [EC:6.2.1.53]
GCM10017557_82750  D-alanine--poly(phosphoribitol) ligase [KO:K21780] [EC:6.2.1.53]
GCM10017557_78160  acyl carrier protein [KO:K21781]
GCM10017557_78270  acyl-CoA dehydrogenase [KO:K21782] [EC:1.3.8.14]
GCM10017557_82740  acyl-CoA dehydrogenase [KO:K21782] [EC:1.3.8.14]
GCM10017557_78280  polyketide synthase [KO:K21783] [EC:2.3.1.-]
GCM10017557_78150  8-amino-7-oxononanoate synthase [KO:K21784]
GCM10017557_78240  RedV protein [KO:K21785]
GCM10017557_78110  methyltransferase [KO:K27675] [EC:2.1.1.-]
GCM10017557_78100  hypothetical protein [KO:K21787]
GCM10017557_57550  ACP S-malonyltransferase [KO:K00645] [EC:2.3.1.39]
GCM10017557_10770  hypothetical protein [KO:K00645] [EC:2.3.1.39]
GCM10017557_78180  fabH3; 3-oxoacyl-[acyl-carrier-protein] synthase 3 protein 3 [KO:K21788]
GCM10017557_26540  oxidoreductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_31320  3-ketoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_35640  fabG; 3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_38580  oxidoreductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_61920  fabG; 3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_64230  oxidoreductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_64470  beta-ketoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_69910  3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_70890  fabG; 3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_73850  hypothetical protein [KO:K00059] [EC:1.1.1.100]
GCM10017557_01000  oxidoreductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_01350  L-xylulose reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_79410  3-ketoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_80060  short-chain dehydrogenase [KO:K00059] [EC:1.1.1.100]
GCM10017557_80760  3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_04030  beta-ketoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_81400  short-chain dehydrogenase [KO:K00059] [EC:1.1.1.100]
GCM10017557_14890  3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
GCM10017557_21480  fabG; 3-oxoacyl-[acyl-carrier-protein] reductase FabG [KO:K00059] [EC:1.1.1.100]
GCM10017557_78200  3-oxoacyl-[acyl-carrier-protein] synthase 2 [KO:K21789]
GCM10017557_78190  acyl carrier protein [KO:K21790]
GCM10017557_78170  acyl carrier protein [KO:K21790]
GCM10017557_78120  thioesterase [KO:K21791]
GCM10017557_78130  hypothetical protein [KO:K21792 K21793]
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
sgm00330  Arginine and proline metabolism
sgm00620  Pyruvate metabolism
KO pathway
ko00333   
LinkDB

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