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Results 1 - 6 of 6
EC Number
Reaction
Commentary
Reference
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O
FADH2 and O2 form an 4alpha-FAD-OOH intermediate that decays to 4alpha-FAD-OH. Tryptophan likely does not react directly with any flavin intermediate. Substrate chlorination occurs after completion of the flavin redox reactions
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O
FADH2 reacts with O2 to make peroxyflavin, which is decomposed by Cl-. the resulting HOCl is guided through the tunnel to tryptophan, where it is activated to participate in electrophilic aromatic substitution
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O
monooxygenase-like mechanism proposed. First, FADH2 is produced by a flavin reductase using NADH. FADH2 binds to flavin-free enzyme and reacts to enzyme-bound 4alpha-flavin hydroperoxide which attacks L-tryptophan. Activated tryptophan is attacked by chloride as a nucleophile, the resulting halohydrin is dehydrated to the end product 7-chlorotryptophan
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O
proposed mechanism: after formation of a FAD-OOH intermediate, the reactive chlorine is generated as a FAD-O-Cl intermediate. Chlorination of L-tryptophan proceeds by attack of the aromatic pi electrons on the intermediate in a two-electron mechanism and abstraction of a proton generates the final product
tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O
reaction mechanism
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
Results 1 - 6 of 6