Thyroid peroxidase - can atomic iodine serve as iodinating agent?
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McMurry's Organic Chemistry (7th Ed.) states, that Tyrosine is iodinated by mechanism of electrophilic aromatic substitution and the iodinating agent is I+IX+ or HIOHIO formed by thyroid peroxidase. The mechanism is quite clear in this case.
Wikipedia article about thyroid peroxidase states that:
thyroid peroxidase oxidizes iodide to atomic iodine (II) or iodinium (I+IX+).
From this figure from previous wikipedia article it moreover seems like I0IX0 would be able to function as an iodinating agent.
I would like to ask whether atomic iodine produced by thyroid peroxidase could act as an iodinating agent by itself (if yes, by what mechanism, because I think electrophilic aromatic substitution cannot be used, morover, this reaction is supposed to happen in the colloid without any additional enzymatic support) or if I just didn't understand the article and figure correctly and additional oxidation to I+IX+ is indeed needed (atomic iodine is just an irreactive intermediate).
I tried to find some references for this, but I was unable to do so.
NOTE: I originally posted this in biology.stackexchange.com but got no answers, so I thought here it might be more suitable
Wikipedia article about thyroid peroxidase states that:
thyroid peroxidase oxidizes iodide to atomic iodine (II) or iodinium (I+IX+).
From this figure from previous wikipedia article it moreover seems like I0IX0 would be able to function as an iodinating agent.
I would like to ask whether atomic iodine produced by thyroid peroxidase could act as an iodinating agent by itself (if yes, by what mechanism, because I think electrophilic aromatic substitution cannot be used, morover, this reaction is supposed to happen in the colloid without any additional enzymatic support) or if I just didn't understand the article and figure correctly and additional oxidation to I+IX+ is indeed needed (atomic iodine is just an irreactive intermediate).
I tried to find some references for this, but I was unable to do so.
NOTE: I originally posted this in biology.stackexchange.com but got no answers, so I thought here it might be more suitable
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