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The dipeptide, Gln-Gly, on treatment with CH$$_3$$COCl followed by aqueous work up gives:
The dipeptide is written as
$$H_2N{-}CH(CO{-}NH_2){-}CH_2{-}CH_2{-}C(O)NH{-}CH_2{-}COOH$$
(N-terminus) (peptide bond) (C-terminus)
The two functional groups that can, in principle, react with $$CH_3COCl$$ are
1. the free α-amino group at the N-terminus, $$H_2N{-}$$
2. the terminal carboxylic acid group, $${-}COOH$$.
Facts to remember
• Acyl chlorides acylate a free amine easily, giving an amide (acetylation).
• Carboxylic acids can form mixed anhydrides with $$CH_3COCl$$, but these anhydrides are hydrolysed back to the parent acid during the aqueous work-up.
• The nitrogens already present in amide linkages (peptide bond and$$-CONH_2$$ side chain of Gln) are far too weakly nucleophilic to be acylated under these mild conditions.
Step-wise reaction
$$H_2N{-}$$ of Gln attacks the carbonyl carbon of $$CH_3COCl \; \rightarrow$$ tetrahedral intermediate $$\rightarrow$$ loss of $$Cl^-$$ gives the N-acetylated amide.
No lasting change occurs at the carboxyl terminus; any transient anhydride is hydrolysed in the work-up to regenerate $$-COOH$$.
Hence the only permanent change is replacement of the N-terminal hydrogen by an acetyl group.
Product (Option A):
$$CH_3CONH{-}CH(CO{-}NH_2){-}CH_2{-}CH_2{-}C(O)NH{-}CH_2{-}COOH$$
Therefore, the dipeptide Gln-Gly gives its N-acetyl derivative on treatment with $$CH_3COCl$$ followed by water.
Option A which is: the N-acetylated dipeptide (Ac-Gln-Gly).
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