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Why will Gly-Met-Gly react with cyanogen bromide, but Gly-Cys-Gly will not react with cyanogen bromide?
I. There would be a highly strained four-membered ring intermediate in the case of cysteine.
II. After the addition of the thiol of cysteine to the cyano-group, a stable thioether will be formed, which does not react any further.
III. After the addition of the thiol of cysteine to the bromo-cation, a stable thioether will be formed, which does not react any further.
IV. Cysteine cannot form a stable bromonium-ion intermediate.
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