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Biomolecules question

2025 · 4 Apr · Shift 2 · Q19
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Biomolecules question

2025 · 4 Apr · Shift 2 · Q19

JEE MainChemistryBiomoleculesMCQ+4 / −1
A dipeptide, " xxx" on complete hydrolysis gives "yyy" and "zzz". "yyy" on treatment with aq. HNO2\mathrm{HNO}_2HNO2​ produces lactic acid. On the other hand " z " on heating gives the following cyclic molecule. JEE Main 2025 (Online) 4th April Evening Shift Chemistry - Biomolecules Question 4 English Based on the information given, the dipeptide XXX is :
  1. A
    alanine-alanine
  2. B
    valine-glycine
  3. C
    valine-leucine
  4. D
    alanine-glycine
View written solutionFree

Correct answer: D

  1. Identify amino acid yyy from reaction with nitrous acid

A primary amino acid on treatment with aqueous HNO2\mathrm{HNO_2}HNO2​ gives the corresponding α\alphaα-hydroxy acid:

R−CH(NH2)−COOH→HNO2R−CH(OH)−COOHR-CH(NH_2)-COOH \xrightarrow{HNO_2} R-CH(OH)-COOHR−CH(NH2​)−COOHHNO2​​R−CH(OH)−COOH

It is given that yyy gives lactic acid, whose structure is:

CH3−CH(OH)−COOHCH_3-CH(OH)-COOHCH3​−CH(OH)−COOH

So the parent amino acid must be:

CH3−CH(NH2)−COOHCH_3-CH(NH_2)-COOHCH3​−CH(NH2​)−COOH

which is alanine.

Thus,

y=alaniney = \text{alanine}y=alanine
  1. Identify amino acid zzz from the cyclic product on heating

On heating, amino acids can form cyclic anhydride-like products only in special cases. The amino acid that readily gives a simple cyclic product on heating is glycine, which forms a cyclic dipeptide-related product represented in such questions as the six-membered ring derived from glycine units.

Hence,

z=glycinez = \text{glycine}z=glycine
  1. Determine the dipeptide XXX

Since complete hydrolysis of dipeptide XXX gives yyy and zzz, and we found:

y=alanine,z=glyciney = \text{alanine}, \qquad z = \text{glycine}y=alanine,z=glycine

therefore XXX must be the dipeptide made from alanine and glycine.

Among the options, this is:

alanine-glycine\boxed{\text{alanine-glycine}}alanine-glycine​
  1. Check options
  • A: alanine-alanine →\to→ hydrolysis gives only alanine, not glycine. Incorrect.
  • B: valine-glycine →\to→ valine with HNO2\mathrm{HNO_2}HNO2​ would give α\alphaα-hydroxy acid of valine, not lactic acid. Incorrect.
  • C: valine-leucine →\to→ no alanine/glycine. Incorrect.
  • D: alanine-glycine →\to→ matches both observations. Correct.

  1. Comparison with stored answer

Stored correct answer: D

Derived answer: D

They agree.

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