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The starting material is a dipeptide composed of two amino acids: Asparagine (Asn) at the N-terminus and Serine (Ser) at the C-terminus. Combined, they contain several nucleophilic functional groups capable of reacting:
The reagents are acetic anhydride (CH3CO)2O in excess and triethylamine (NEt3) as a base.
This is an acetylation reaction. Acetic anhydride introduces acetyl groups (CH3CO-) to nucleophilic atoms like nitrogen and oxygen. Because it is explicitly added in excess, every nucleophilic group that is strong enough to react will become fully acetylated.
Not all nitrogen and oxygen atoms in a peptide react equally with acetic anhydride. Here is how they behave:
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