Sanger's reagent, DNFB, is known to react with phenolic, imidazole, and free amino groups. With this...

Sanger's reagent, DNFB, is known to react with phenolic, imidazole, and free amino groups. With this in mind, would it be possible to determine the N and C terminals of a dipeptide composed of tyrosine and lysine?

Expert Solution

Sanger’s reagent is 1-fluoro-2,4-dinitrobenzene (FDNB) is known to react with phenolic, imidazole, and free amino groups to yield the corresponding, colored dinitrophenyl (DNP) compounds.
The N-amino group on all amino acids, including lysine, and the hydroxy group on tyrosine, react to form DNP derivatives. If this DNP derivative of dipeptide is hydrolyzed in acid and extracted with ether, all uncharged entities will be extracted into the ether phase while all polar components will remain in the aqueous phase. Thus, the nonpolar N-terminal DNP-amino acids and diDNP-amino acids (from N-terminal lysine, tyrosine) will be removed into the ether phase because their carboxyl groups are protonated (i.e., uncharged).
Once the N-terminal DNP-amino acid derivatives are separated from those DNP-amino acid derivatives that are not the N-terminus amino acid, the DNP-derivatives and free amino acids may be identified by chromatographic techniques.

queen_honey_blossom answered 1 year ago

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