Why are DNP-derivatives used to determine the N terminal amino acid in peptide chains?
Ans. Sanger’s reagent forms covalent exclusively with the amino group of a residue in a peptide chain. Upon hydrolysis with HCl, the 2,4-DNP-N-ter adduct is released from the peptide chain. The resultant adduct is identified using chromatography.
So, DNP can be used to determine the N-ter residue because it has a free amino group.
Demerits of this reagent: DNA reacts with amino groups. So, it may react with non-N-terminal residues having a amino groups, like lysine. However, correlation of the results of various chemical and enzymatic hydrolysis of the peptide yields exclusive result of the N-terminal residue.
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