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Biomolecules question

2020 · Shift 2 · Q5
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Biomolecules question

2020 · Shift 2 · Q5

JEE AdvancedChemistryBiomoleculesNumerical+3 / −1
The structure of a peptide is given below. JEE Advanced 2020 Paper 2 Offline Chemistry - Biomolecules Question 17 English If the absolute values of the net charge of the peptide at pH=2\mathrm{pH}=2pH=2, pH=6\mathrm{pH}=6pH=6, and pH=11\mathrm{pH}=11pH=11 are ∣Z1∣,∣Z2∣\left|Z_1\right|,\left|Z_2\right|∣Z1​∣,∣Z2​∣, and ∣Z3∣\left|Z_3\right|∣Z3​∣, respectively, then what is ∣Z1∣+∣Z2∣+∣Z3∣\left|Z_1\right|+\left|Z_2\right|+\left|Z_3\right|∣Z1​∣+∣Z2​∣+∣Z3​∣?
Numerical answer
View written solutionFree

Correct answer: 5

  1. Identify the ionisable groups in the peptide

    In a peptide, the groups that can contribute to charge are:

    • the N-terminal amino group: can be protonated to −NH3+-\mathrm{NH_3^+}−NH3+​
    • the C-terminal carboxyl group: can be deprotonated to −COO−-\mathrm{COO^-}−COO−
    • any ionisable side chains present in the amino acid residues

    From the given peptide structure, the ionisable side chains are:

    • one basic side chain (like Lys/Arg type) giving +1+1+1 in acidic/neutral medium and becoming neutral only at sufficiently high pH depending on group
    • one acidic side chain (like Asp/Glu type) giving 000 in acidic medium and −1-1−1 in neutral/basic medium

    So effectively, the peptide has these charge-bearing groups:

    • N-terminus: +1+1+1 at low pH
    • C-terminus: −1-1−1 at moderate/high pH
    • one acidic side chain: −1-1−1 at moderate/high pH
    • one basic side chain: +1+1+1 at low/neutral pH
  2. Charge at pH=2\mathrm{pH}=2pH=2

    At very low pH:

    • N-terminus is protonated: +1+1+1
    • basic side chain is protonated: +1+1+1
    • C-terminus is mostly COOH\mathrm{COOH}COOH: 000
    • acidic side chain is mostly COOH\mathrm{COOH}COOH: 000

    Hence, Z1=+2Z_1 = +2Z1​=+2 so, ∣Z1∣=2|Z_1|=2∣Z1​∣=2

  3. Charge at pH=6\mathrm{pH}=6pH=6

    Around neutral pH:

    • N-terminus remains protonated: +1+1+1
    • basic side chain remains protonated: +1+1+1
    • C-terminus is deprotonated: −1-1−1
    • acidic side chain is deprotonated: −1-1−1

    Therefore, Z2=(+1)+(+1)+(−1)+(−1)=0Z_2 = (+1)+(+1)+(-1)+(-1)=0Z2​=(+1)+(+1)+(−1)+(−1)=0 so, ∣Z2∣=0|Z_2|=0∣Z2​∣=0

  4. Charge at pH=11\mathrm{pH}=11pH=11

    At high pH:

    • N-terminus becomes largely deprotonated: 000
    • C-terminus remains −1-1−1
    • acidic side chain remains −1-1−1
    • basic side chain loses proton and becomes neutral: 000

    Thus, Z3=−2Z_3 = -2Z3​=−2 so, ∣Z3∣=2|Z_3|=2∣Z3​∣=2

  5. Required sum

    ∣Z1∣+∣Z2∣+∣Z3∣=2+0+2=4|Z_1|+|Z_2|+|Z_3| = 2+0+2 = 4∣Z1​∣+∣Z2​∣+∣Z3​∣=2+0+2=4

  6. Comparison with stored answer

    The derived answer is 444, whereas the stored correct answer is 555.

    Hence, I do not agree with the stored answer.

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