Vasopressin, a nonapeptide hormone secreted by the pituitary gland, functions by stimulating the kidney to retain water. Its sequence was determined by the following evidence: 1. Vasopressin is a cyclic compound containing a disulfide bridge between two cysteine residues. 2. When the disulfide bridge is reduced, vasopressin has the constitution Arg, Asn, Cys2, Gln, Gly, Ile, Phe, Pro. 3. Partial hydrolysis of vasopressin yields seven fragments: Asp-Cys, Ile-Glu, Cys-Phe, Arg-Gly, Phe-Ile-Glu, Glu-Asp-Cys, Cys-Pro-Arg. 4. Gly is the C-terminal group. 5. Both Glu and Asp are present as their side chain amides (Gln and Asn) rather than as free side-chain acids. From the above information, determine the primary sequence of vasopressin and then draw the structure of the Phe-Ile-Glu fragment as it would exist in the intact peptide.

Biochemistry
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Vasopressin, a nonapeptide hormone secreted by the pituitary gland, functions by stimulating the kidney to retain water. Its sequence was determined by the following evidence:
1. Vasopressin is a cyclic compound containing a disulfide bridge between two cysteine residues.
2. When the disulfide bridge is reduced, vasopressin has the constitution Arg, Asn, Cys2, Gln, Gly, Ile, Phe, Pro.
3. Partial hydrolysis of vasopressin yields seven fragments: Asp-Cys, Ile-Glu, Cys-Phe, Arg-Gly, Phe-Ile-Glu, Glu-Asp-Cys, Cys-Pro-Arg.
4. Gly is the C-terminal group.
5. Both Glu and Asp are present as their side chain amides (Gln and Asn) rather than as free side-chain acids.

From the above information, determine the primary sequence of vasopressin and then draw the structure of the Phe-Ile-Glu fragment as it would exist in the intact peptide.

 
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