KEGG   PATHWAY: serf00333
Entry
serf00333                   Pathway                                
Name
Prodigiosin biosynthesis - Serratia sp. FS14
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
serf00333  Prodigiosin biosynthesis
serf00333

Module
serf_M00837  Prodigiosin biosynthesis, L-proline => prodigiosin [PATH:serf00333]
Organism
Serratia sp. FS14 [GN:serf]
Gene
L085_23045  biosynthesis protein PigD [KO:K21428] [EC:2.2.1.12]
L085_23050  aminotransferase [KO:K21778] [EC:2.6.1.-]
L085_23035  biosynthesis protein PigB [KO:K21779]
L085_23070  L-prolyl-AMP ligase [KO:K21780] [EC:6.2.1.53]
L085_23060  peptidyl carrier protein [KO:K21781]
L085_23030  acyl-CoA dehydrogenase [KO:K21782] [EC:1.3.8.14]
L085_23075  beta-ketomyristol-ACP synthase [KO:K21783] [EC:2.3.1.-]
L085_23065  aminotransferase [KO:K21784]
L085_23090  prodigiosin biosynthesis protein PigM [KO:K21785]
L085_23055  O-methyl transferase [KO:K21786] [EC:2.1.1.-]
L085_23040  putative phosphoenolpyruvate-utilizing enzyme [KO:K21787]
L085_19190  malonyl-CoA-[acyl-carrier-protein] transacylase [KO:K00645] [EC:2.3.1.39]
L085_09440  short-chain dehydrogenase/reductase [KO:K00059] [EC:1.1.1.100]
L085_19185  fabG; 3-ketoacyl-(acyl-carrier-protein) reductase [KO:K00059] [EC:1.1.1.100]
L085_13670  oxidoreductase, short chain dehydrogenase/reductase family protein [KO:K00059] [EC:1.1.1.100]
L085_01205  3-ketoacyl-(acyl-carrier-protein) reductase [KO:K00059] [EC:1.1.1.100]
L085_06195  putative oxidoreductase [KO:K00059] [EC:1.1.1.100]
L085_16805  short-chain dehydrogenase/reductase SDR [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
serf00330  Arginine and proline metabolism
serf00620  Pyruvate metabolism
KO pathway
ko00333   
LinkDB

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