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2018 H2 Chem P1 Q30 — Nitrogen Compound Solution

Nitrogen Compound 2018 A-Level H2 Chemistry · Paper 1 · Q30

Question

A pentapeptide is heated under reflux with 6 mol dm\(^{-3}\) HCl.
Partial hydrolysis occurs resulting in the production of a mixture of smaller peptides and amino acids, which include the four fragments shown.
What is the formula of the pentapeptide?Question diagram
  1. AA
  2. BB
  3. CC
  4. DD
Correct answer: D

Video Solution

Explanation

The answer is D.
Each fragment shows two amino acids that are next to each other in the chain, read from the \(\text{NH}_2\) end (N-terminus) to the \(\text{CO}_2\text{H}\) end:
• Fragment 1: Ser-Gly (serine, \(\text{CH}_2\text{OH}\) side chain, then glycine)
• Fragment 2: Ala-Ser (alanine, \(\text{CH}_3\) side chain, then serine)
• Fragment 3: Ser-Ala
• Fragment 4: Gly-Lys (lysine, \((\text{CH}_2)_4\text{NH}_2\) side chain)
Linking the overlaps: Ser-Ala (3), Ala-Ser (2), Ser-Gly (1), Gly-Lys (4) gives Ser-Ala-Ser-Gly-Lys, which is pentapeptide D. Its four adjacent pairs are exactly the four fragments.
• A is wrong: A is Ala-Ser-Ser-Gly-Lys. Its adjacent pairs are Ala-Ser, Ser-Ser, Ser-Gly and Gly-Lys, so it cannot give fragment 3 (Ser-Ala).
• B is wrong: B is Ser-Gly-Lys-Ala-Gly. Its pairs are Ser-Gly, Gly-Lys, Lys-Ala and Ala-Gly, so it cannot give fragment 2 (Ala-Ser) or fragment 3 (Ser-Ala).
• C is wrong: C is Ala-Ser-Gly-Lys-Gly. Its pairs are Ala-Ser, Ser-Gly, Gly-Lys and Lys-Gly, so it cannot give fragment 3 (Ser-Ala).

Worked solution diagram

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