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Question

A tetrapeptide, made up of natural amino acids, has alanine as the N-terminal residue which is coupled to a chiral amino acid. Upon complete hydrolysis, the tetrapeptide gives glycine, alanine, phenylalanine and leucine. The number of possible sequences of the tetrapeptide is ____________

Amino Acid Identification and Chirality

The tetrapeptide is composed of four specific amino acids obtained upon hydrolysis: Glycine (Gly), Alanine (Ala), Phenylalanine (Phe), and Leucine (Leu).

  • Glycine (Gly): Achiral (alpha-carbon has two hydrogen atoms).
  • Alanine (Ala): Chiral.
  • Phenylalanine (Phe): Chiral.
  • Leucine (Leu): Chiral.

Applying Sequence Constraints

The sequence must satisfy two main conditions:

  1. The N-terminal residue is Alanine (Ala). This fixes the first amino acid in the sequence. Sequence structure: $Ala - AA2 - AA3 - AA4$.
  2. Alanine is coupled to a chiral amino acid. This means the second amino acid (AA2) must be chiral.

Determining Possible Sequences

The available amino acids for positions AA2, AA3, and AA4 are {Gly, Phe, Leu}.

Considering the chiral constraint for AA2:

  • The chiral amino acids available for AA2 are Phe and Leu. Gly is achiral and cannot be placed at AA2.

Case 1: AA2 is Phenylalanine (Phe)

  • Sequence starts: $Ala - Phe - ...$
  • Remaining amino acids for AA3 and AA4: {Gly, Leu}.
  • Possible arrangements: $Gly - Leu$ or $Leu - Gly$.
  • Resulting sequences: $Ala-Phe-Gly-Leu$ and $Ala-Phe-Leu-Gly$. (2 possibilities)

Case 2: AA2 is Leucine (Leu)

  • Sequence starts: $Ala - Leu - ...$
  • Remaining amino acids for AA3 and AA4: {Gly, Phe}.
  • Possible arrangements: $Gly - Phe$ or $Phe - Gly$.
  • Resulting sequences: $Ala-Leu-Gly-Phe$ and $Ala-Leu-Phe-Gly$. (2 possibilities)

Calculating Total Number of Sequences

The total number of possible sequences is the sum of possibilities from Case 1 and Case 2.

Total Sequences = (Possibilities with Phe at AA2) + (Possibilities with Leu at AA2)

Total Sequences = 2 + 2 = 4

Therefore, there are 4 possible sequences for the tetrapeptide.

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Important Questions from Peptides

  1. Partial hydrolysis of a pentapeptide yields all possible tripeptides and dipeptides. The dipeptides that are obtained upon hydrolysis are given below.


    Val-Ala, Gln-His, Phe-Val and Ala-Gln

    The total number of tripeptides obtained that contain 'Ala' as one of the amino acids is ________ (in integer).

  2. The structure of the dipeptide Ala-Pro derived from the natural amino acids is
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