KEGG   PATHWAY: slf00333
Entry
slf00333                    Pathway                                
Name
Prodigiosin biosynthesis - Streptomyces liliifuscus
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
slf00333  Prodigiosin biosynthesis
slf00333

Organism
Streptomyces liliifuscus [GN:slf]
Gene
JEQ17_02545  amino acid adenylation domain-containing protein [KO:K21780] [EC:6.2.1.53]
JEQ17_02535  acyl carrier protein [KO:K21781]
JEQ17_02480  acyl-CoA dehydrogenase family protein [KO:K21782] [EC:1.3.8.14]
JEQ17_02475  polyketide synthase [KO:K21783] [EC:2.3.1.-]
JEQ17_02540  aminotransferase class I/II-fold pyridoxal phosphate-dependent enzyme [KO:K21784]
JEQ17_02495  RedV protein [KO:K21785]
JEQ17_02560  methyltransferase domain-containing protein [KO:K21786] [EC:2.1.1.-]
JEQ17_02565  phosphoenolpyruvate-utilizing enzyme [KO:K21787]
JEQ17_40335  peptidyl-prolyl cis-trans isomerase [KO:K00645] [EC:2.3.1.39]
JEQ17_40495  ACP S-malonyltransferase [KO:K00645] [EC:2.3.1.39]
JEQ17_32060  ACP S-malonyltransferase [KO:K00645] [EC:2.3.1.39]
JEQ17_02525  ketoacyl-ACP synthase III [KO:K21788]
JEQ17_39130  fabG; 3-oxoacyl-ACP reductase FabG [KO:K00059] [EC:1.1.1.100]
JEQ17_39475  SDR family oxidoreductase [KO:K00059] [EC:1.1.1.100]
JEQ17_49330  beta-ketoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
JEQ17_03845  fabG; 3-oxoacyl-ACP reductase FabG [KO:K00059] [EC:1.1.1.100]
JEQ17_07140  SDR family oxidoreductase [KO:K00059] [EC:1.1.1.100]
JEQ17_10940  SDR family oxidoreductase [KO:K00059] [EC:1.1.1.100]
JEQ17_13685  SDR family oxidoreductase [KO:K00059] [EC:1.1.1.100]
JEQ17_20350  SDR family oxidoreductase [KO:K00059] [EC:1.1.1.100]
JEQ17_24400  fabG; 3-oxoacyl-ACP reductase FabG [KO:K00059] [EC:1.1.1.100]
JEQ17_26810  3-oxoacyl-ACP reductase [KO:K00059] [EC:1.1.1.100]
JEQ17_34395  SDR family oxidoreductase [KO:K00059] [EC:1.1.1.100]
JEQ17_35825  SDR family oxidoreductase [KO:K00059] [EC:1.1.1.100]
JEQ17_35960  fabG; 3-oxoacyl-[acyl-carrier-protein] reductase [KO:K00059] [EC:1.1.1.100]
JEQ17_02515  beta-ketoacyl-[acyl-carrier-protein] synthase family protein [KO:K21789]
JEQ17_02520  acyl carrier protein [KO:K21790]
JEQ17_02530  acyl carrier protein [KO:K21790]
JEQ17_02555  thioesterase [KO:K21791]
JEQ17_02550  aminotransferase class I/II-fold pyridoxal phosphate-dependent enzyme [KO:K21792]
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
slf00330  Arginine and proline metabolism
slf00620  Pyruvate metabolism
KO pathway
ko00333   
LinkDB

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