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Biomolecules question

2018 · 15 Apr · Shift 2 · Q4
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Biomolecules question

2018 · 15 Apr · Shift 2 · Q4

JEE MainChemistryBiomoleculesMCQ+4 / −1
The dipeptide, Gln-Gly, on treatment with CH3COClCH_3COClCH3​COCl followed y aqueous work up gives :
  1. A
    JEE Main 2018 (Online) 15th April Evening Slot Chemistry - Biomolecules Question 156 English Option 1
  2. B
    JEE Main 2018 (Online) 15th April Evening Slot Chemistry - Biomolecules Question 156 English Option 2
  3. C
    JEE Main 2018 (Online) 15th April Evening Slot Chemistry - Biomolecules Question 156 English Option 3
  4. D
    JEE Main 2018 (Online) 15th April Evening Slot Chemistry - Biomolecules Question 156 English Option 4
View written solutionFree

Correct answer: C

  1. Identify the peptide structure

The dipeptide Gln-Gly means:

  • N-terminal amino acid = Glutamine (Gln)
  • C-terminal amino acid = Glycine (Gly)

So the peptide skeleton is:

H2N−CH(CH2CH2CONH2)−CO−NH−CH2−COOHH_2N-CH(CH_2CH_2CONH_2)-CO-NH-CH_2-COOHH2​N−CH(CH2​CH2​CONH2​)−CO−NH−CH2​−COOH

  1. Reagent used: CH3COClCH_3COClCH3​COCl followed by aqueous work-up

Acetyl chloride reacts readily with free amino groups to give N-acetyl derivatives.

In this dipeptide, the functional groups are:

  • free N-terminal amino group: −NH2-NH_2−NH2​
  • one peptide linkage: −CO−NH−-CO-NH-−CO−NH−
  • side-chain amide of glutamine: −CONH2-CONH_2−CONH2​
  • terminal carboxylic acid: −COOH-COOH−COOH
  1. Which group will react?

The most reactive site toward acetyl chloride here is the free amino group at the N-terminus.

Thus,

−NH2→CH3COCl−NHCOCH3-NH_2 \xrightarrow{CH_3COCl} -NHCOCH_3−NH2​CH3​COCl​−NHCOCH3​

The peptide amide nitrogen and glutamine side-chain amide are not acetylated under this simple treatment because amide nitrogens are much less nucleophilic.

  1. Product formed

Therefore the product is the N-acetyl derivative of Gln-Gly:

CH3CO−NH−CH(CH2CH2CONH2)−CO−NH−CH2−COOHCH_3CO-NH-CH(CH_2CH_2CONH_2)-CO-NH-CH_2-COOHCH3​CO−NH−CH(CH2​CH2​CONH2​)−CO−NH−CH2​−COOH

  1. Conclusion

So the correct option must be the one showing acetylation of only the terminal amino group.

Hence, the answer is Option C.

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