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Literature summary extracted from

  • Dorrestein, P.; Yeh, E.; Garneau-Tsodikova, S.; Kelleher, N.; Walsh, C.
    Dichlorination of a pyrrolyl-S-carrier protein by FADH2- dependent halogenase PltA during pyoluteorin biosynthesis (2005), Proc. Natl. Acad. Sci. USA, 102, 13843-13848 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.19.56 expression in Escherichia coli Pseudomonas fluorescens

Organism

EC Number Organism UniProt Comment Textmining
1.14.19.56 Pseudomonas fluorescens Q4KCZ0
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-
1.14.19.56 Pseudomonas fluorescens ATCC BAA-477 Q4KCZ0
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-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.19.56 recombinant protein Pseudomonas fluorescens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.19.56 1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FADH2 + 2 bromide + 2 O2
-
 Pseudomonas fluorescens 4,5-dibromo-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FAD + 4 H2O
-
 ?
1.14.19.56 1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FADH2 + 2 bromide + 2 O2
-
 Pseudomonas fluorescens ATCC BAA-477 4,5-dibromo-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FAD + 4 H2O
-
 ?
1.14.19.56 1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FADH2 + 2 chloride + 2 O2
-
 Pseudomonas fluorescens 4,5-dichloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FAD + 4 H2O
-
 ?
1.14.19.56 1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FADH2 + 2 chloride + 2 O2
-
 Pseudomonas fluorescens ATCC BAA-477 4,5-dichloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + 2 FAD + 4 H2O
-
 ?
1.14.19.56 1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FADH2 + chloride + O2
-
 Pseudomonas fluorescens 5-chloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FAD + 2 H2O
-
 ?
1.14.19.56 1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FADH2 + chloride + O2
-
 Pseudomonas fluorescens ATCC BAA-477 5-chloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FAD + 2 H2O
-
 ?
1.14.19.56 5-chloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FADH2 + chloride + O2
-
 Pseudomonas fluorescens 4,5-dichloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FAD + H2O
-
 ?
1.14.19.56 5-chloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FADH2 + chloride + O2
-
 Pseudomonas fluorescens ATCC BAA-477 4,5-dichloro-1H-pyrrole-2-carbonyl-[PltL peptidyl-carrier protein] + FAD + H2O
-
 ?
1.14.19.56 additional information halogenase PltA catalyzes chlorination at both positions of the ring, generating the 5-chloropyrrolyl-S-PltL intermediate and then the 4,5-dichloropyrrolyl-S-PltL product. The regiospecific chlorination occurs at position 5 and then position 4 of the heteroaromatic ring. The mechanism may involve formation of a FAD-4a-OCl intermediate for capture by the electron-rich C4 and C5 of the heteroaromatic pyrrole moiety Pseudomonas fluorescens ?
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 ?
1.14.19.56 additional information halogenase PltA catalyzes chlorination at both positions of the ring, generating the 5-chloropyrrolyl-S-PltL intermediate and then the 4,5-dichloropyrrolyl-S-PltL product. The regiospecific chlorination occurs at position 5 and then position 4 of the heteroaromatic ring. The mechanism may involve formation of a FAD-4a-OCl intermediate for capture by the electron-rich C4 and C5 of the heteroaromatic pyrrole moiety Pseudomonas fluorescens ATCC BAA-477 ?
-
 ?

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.19.56 FAD purified PltA contains tightly bound FAD Pseudomonas fluorescens

General Information

EC Number General Information Comment Organism
1.14.19.56 physiological function the antifungal natural product pyoluteorin contains a 4,5-dichloropyrrole moiety. Dichlorination in the heteroaromatic ring occurs after proline is tethered by thioester linkage to the carrier protein PltL and enzymatically desaturated to the pyrrolyl-S-PltL. The FADH2-dependent halogenase PltA catalyzes chlorination at both positions of the ring, generating the 5-chloropyrrolyl-S-PltL intermediate and then the 4,5-dichloropyrrolyl-S-PltL product. PltA activity strictly depends on a heterologous flavin reductase that uses NAD(P)H to produce FADH2 Pseudomonas fluorescens