A pentapeptide was converted to its DNP derivative, then completely hydrolyzed and analyzed quantitatively. It gave DNP-methionine,

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A pentapeptide was converted to its DNP derivative, then completely hydrolyzed and analyzed quantitatively. It gave DNP-methionine, 2 moles of methionine, and 1 mole each of serine and glycine. The peptide was then partially hydrolyzed, the fragments were converted to their DNP derivatives, and each of them was hydrolyzed and analyzed quantitatively. Two tripeptides and two dipeptides isolated in this way gave the following products:
Tripeptide A: DNP-methionine and 1 mole each of methionine and glycine
Tripeptide B: DNP-methionine and 1 mole each of methionine and serine
Dipeptide C: DNP-methionine and 1 mole of methionine
Dipeptide D: DNP-serine and 1 mole of methionine
Deduce the structure of the original pentapeptide, and explain your reasoning.
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Organic Chemistry A Short Course

ISBN: 978-1111425562

13th edition

Authors: Harold Hart, Christopher M. Hadad, Leslie E. Craine, David J. Hart

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