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Literature summary for 1.14.19.9 extracted from

  • Karabencheva-Christova, T.G.; Torras, J.; Mulholland, A.J.; Lodola, A.; Christov, C.Z.
    Mechanistic insights into the reaction of chlorination of tryptophan catalyzed by tryptophan 7-halogenase (2017), Sci. Rep., 7, 17395 .
    View publication on PubMedView publication on EuropePMC
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Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
tryptophan + FADH2 + chloride + O2 + H+ Pseudomonas fluorescens
-
 7-chloro-L-tryptophan + FAD + 2 H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Pseudomonas fluorescens P95480
-
-

Reaction

Reaction Comment Organism Reaction ID
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O reaction mechanism, combined quantum mechanical/molecular mechanical (QM/MM) calculations of potential energy and free energy surfaces, using the structure, PDB ID 2AR8, and employing density functional theory. First reaction step is the formation of an arenium ion (Wheland intermediate), the second reaction step is the deprotonation of the Wheland intermediate by residue E346 oxygen, at the final stage of the mechanism residues K79 and E346 are regenerated Pseudomonas fluorescens
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
tryptophan + FADH2 + chloride + O2 + H+
-
 Pseudomonas fluorescens 7-chloro-L-tryptophan + FAD + 2 H2O
-
 ?

Synonyms

Synonyms Comment Organism
PrnA
-
 Pseudomonas fluorescens

Cofactor

Cofactor Comment Organism Structure
FAD
-
 Pseudomonas fluorescens

General Information

General Information Comment Organism
metabolism tryptophan 7-halogenase catalyzes chlorination of free tryptophan to 7-chlorotryptophan, which is the first step in the antibiotic pyrrolnitrin biosynthesis Pseudomonas fluorescens