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Literature summary 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

Natural Substrates/ Products (Substrates)

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

Organism

EC Number Organism UniProt Comment Textmining
1.14.19.9 Pseudomonas fluorescens P95480
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
1.14.19.9 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)

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

Synonyms

EC Number Synonyms Comment Organism
1.14.19.9 PrnA
-
 Pseudomonas fluorescens

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.19.9 FAD
-
 Pseudomonas fluorescens

General Information

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