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  1. Problems
  2. /Three amino acids have no ionisable side chain…
EasyChemistryHigh School (11–12)Organic Compounds with Functional Groups › BiomoleculesNumerical

Three amino acids have no ionisable side chain…

StemPy LabContributed by StemPy Lab

Try it on paper first. A hint, the key idea and the worked solution are here when you need them.

Three amino acids have no ionisable side chain. Serine has pK1=2.21\text{p}K_1 = 2.21pK1​=2.21 and pK2=9.15\text{p}K_2 = 9.15pK2​=9.15. Leucine has pK1=2.36\text{p}K_1 = 2.36pK1​=2.36 and pK2=9.60\text{p}K_2 = 9.60pK2​=9.60. Threonine has pK1=2.09\text{p}K_1 = 2.09pK1​=2.09 and pK2=9.10\text{p}K_2 = 9.10pK2​=9.10. Find the isoelectric point of each.

Check your answer

Work it out on paper, then type your number. The answer itself stays hidden.

Need a reminder? The key ideaShowHide

The isoelectric point is the pH at which the average charge is zero. For a neutral side chain, pI=(pK1+pK2)/2\text{pI} = (\text{p}K_1 + \text{p}K_2)/2pI=(pK1​+pK2​)/2. For other amino acids, average the two pK values on either side of the neutral form. The fraction of a group that is still protonated is 11+10pH−pK\dfrac{1}{1 + 10^{\text{pH} - \text{p}K}}1+10pH−pK1​ for a group that is positive when protonated.

The worked solution

Have you tried it?

Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.

Plan. The neutral zwitterion is the main form between pK1\text{p}K_1pK1​ and pK2\text{p}K_2pK2​, so pI is their mean.

Step 1. Serine. (2.21+9.15)/2=5.68(2.21 + 9.15)/2 = 5.68(2.21+9.15)/2=5.68.

Step 2. Leucine. (2.36+9.60)/2=5.98(2.36 + 9.60)/2 = 5.98(2.36+9.60)/2=5.98.

Step 3. Threonine. (2.09+9.10)/2=5.595(2.09 + 9.10)/2 = 5.595(2.09+9.10)/2=5.595, which is 5.605.605.60.

Answer: pI of serine 5.68, of leucine 5.98 and of threonine 5.60.

Check. All three are close to 6, as for glycine. Amino acids with a neutral side chain have similar pI values.

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  1. Amino acids, zwitterions and the isoelectric pointAmino Acids, Peptides, Proteins and Enzymes

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