A threonine residue can be alkylated during an alkylation process using iodoacetamide if overalkylation occurs in the protein?
This reaction does not appear to be mentioned as far as I can find, although a reaction with methionine was mentioned (http://www.ncbi.nlm.nih.gov/pubmed/15912474). And of course, iodoacetamide is usually used to a alkylate cysteine.
Every Protein is different, but, yes threonine residues can be derivitised with iodoacetamide, but in an unfolded polypeptide the reaction is much slower than with free cystine SH and serine OH. You have to lengthen the incubation time but I should imagine that even under normal conditions you might find some small amount of threonine alkylation.
However if you are derivatising a folded protein the answer is dependent on a multitude of factors (H-bonding, surface exposure, etc). A surface threonine may react faster than a buried (H-bonded serine) . There are a few examples in the literature of extremly reactive N terminal threonine residues.
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