Draw the structure of the first non-peptide product released upon trifluoroacetic acid treatment in the Edman degradation of the peptide Asn-Val-Trp-Met-Gly-Arg.

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Answer:

The structure of the first non-peptide product is attached with this answer.

Explanation:

Labelling: Pehr Edman devised a method for labeling the amino-terminal residue and cleaving it from the peptide without disrupting the peptide bonds between the other amino acid residues. The Edman degradation sequentially removes one residue at a time from the amino end of a peptide (Figure attached). Phenyl isothiocyanate reacts with the uncharged terminal amino group of the peptide to form a phenylthiocarbamoyl derivative. Then, under mildly acidic conditions, a cyclic derivative of the terminal amino acid is liberated, which leaves an intact peptide shortened by one amino acid. The cyclic compound is a phenylthiohydantoin (PTH)-amino acid, which can be identified by chromatographic procedures. The Edman procedure can then be repeated on the shortened peptide, yielding another PTH-amino acid, which can again be identified by chromatography. Three more rounds of the Edman degradation will reveal the complete sequence of the original peptide pentapeptide.

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