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Biomolecules question

2023 · 12 Apr · Shift 1 · Q14
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Biomolecules question

2023 · 12 Apr · Shift 1 · Q14

JEE MainChemistryBiomoleculesNumerical+4 / −1
In an oligopeptide named Alanylglycylphenyl alanyl isoleucine, the number of sp2\mathrm{sp}^{2}sp2 hybridised carbons is ‾\underline{\hspace{2cm}}​.
Numerical answer
View written solutionFree

Correct answer: 11

  1. Interpret the peptide name

The oligopeptide is: Alanylglycylphenyl alanyl isoleucine\text{Alanylglycylphenyl alanyl isoleucine}Alanylglycylphenyl alanyl isoleucine

This corresponds to the sequence: Ala−Gly−Phe−Ala−Ile\text{Ala} - \text{Gly} - \text{Phe} - \text{Ala} - \text{Ile}Ala−Gly−Phe−Ala−Ile

So, it is a pentapeptide containing 5 amino acid residues:

  • Alanine
  • Glycine
  • Phenylalanine
  • Alanine
  • Isoleucine

  1. Count the carbonyl carbons in the peptide

Each amino acid residue contributes one carbonyl carbon in the peptide backbone.

A pentapeptide has:

  • 4 peptide bonds, and
  • 1 terminal carboxyl group

But total carbonyl carbons remain equal to the number of residues: 555

Each carbonyl carbon (C=O)(C=O)(C=O) is sp2sp^2sp2 hybridised.

So from the backbone, number of sp2sp^2sp2 carbons = 555


  1. Check side chains for additional sp2sp^2sp2 carbons

Now inspect each side chain:

  • Alanine side chain: −CH3-CH_3−CH3​
    No sp2sp^2sp2 carbon.

  • Glycine side chain: −H-H−H
    No carbon.

  • Phenylalanine side chain: −CH2−C6H5-CH_2-C_6H_5−CH2​−C6​H5​
    The benzene ring has 6 carbons, and all are sp2sp^2sp2 hybridised.

  • Alanine side chain: −CH3-CH_3−CH3​
    No sp2sp^2sp2 carbon.

  • Isoleucine side chain: alkyl group
    No sp2sp^2sp2 carbon.

So additional sp2sp^2sp2 carbons from side chains = 666


  1. Total number of sp2sp^2sp2 hybridised carbons

Total sp2 carbons=5+6=11\text{Total } sp^2 \text{ carbons} = 5 + 6 = 11Total sp2 carbons=5+6=11


  1. Compare with stored answer

Stored correct answer is: 101010

But the correct count is: 111111

Reason: all 5 carbonyl carbons are sp2sp^2sp2, and the phenyl ring contributes 6 more sp2sp^2sp2 carbons.

Hence the stored answer appears to be incorrect.

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