Biomolecules and Chemistry in Everyday Life - Result Question 30

31. A tetrapeptide has $- COOH$ group on alanine. This produces glycine (Gly), valine (Val), phenyl alanine (Phe) and alanine (Ala), on complete hydrolysis. For this tetrapeptide, the number of possible sequences (primary structures) with $-NH _2$ group attached to a chiral centre is

(2013 Adv.)

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Answer:

Correct Answer: 31. $(4)$

Solution:

  1. PLAN: A peptide linkage is hydrolysed to two free amino acids.

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$C^{*}$ is chiral carbon tetrapeptide has four amino acids joined by three peptide linkage.

$-COOH$ group is on alanine part, thus it is at fixed $C-$ terminal position in each combination.

Glycine is optically inactive thus it cannot be on the $N-$ terminal side. Thus, possible combinations are

Phe-Gly-Val-Ala,

Phe-Val-Gly-Ala,

Val-Gly-Phe-Ala,

Val-Phe-Gly-Ala

Thus, in all four combinations are possible.