The substituents R1 and R2 for nine peptides are listed in the table given below. How many of these peptides are positively charged at pH = 7.0 ?
Peptide | R1 | R2 |
I | H | H |
II | H | CH3 |
III | CH2COOH | H |
IV | CH2CONH2 | (CH2)4 NH2 |
V | CH2CONH2 | CH2CONH2 |
VI | (CH2)4 NH2 | (CH2)4 NH2 |
VII | CH2COOH | CH2CONH2 |
VIII | CH2OH | (CH2)4 NH2 |
IX | (CH2)4 NH2 | CH3 |
Any amino acid will exist in a cationic form in solution of pH < pI (isoelectric point)
pH = 7 is less than pI given which implies pI > 7 basic amino acid.
Given peptide will have basic nature if number of basic sites are greater than acidic sites.
Peptide IV R1 = CH2CONH2 R2 = (CH2)4NH2
Peptide VI R1 = (CH2)4NH2 R2 = (CH2)4NH2
Peptide VIII R1 = CH2OH R2 = (CH2)4NH2
peptide IX R1 = (CH2)4NH2 R2 = CH3
This question involves determining the charge of peptides at pH 7.0 based on their side chains (R groups). At pH 7.0, which is neutral, the charge of a peptide depends on the ionization states of its acidic and basic groups.
The general structure given is a dipeptide with two variable substituents R1 and R2. Each peptide also has a free amino group (NH2) at the N-terminus and a free carboxylic acid group (COOH) at the C-terminus. These terminal groups can ionize:
Additionally, the side chains R1 and R2 may contain ionizable groups that affect the overall charge.
Key ionizable groups and their behavior at pH 7.0:
Step-by-step analysis for each peptide:
For each peptide, we must consider the charges from:
Detailed peptide analysis:
Final Answer: Peptides IV, VI, VIII, and IX are positively charged. So, the number is 4.
Isoelectric Point (pI): The pH at which a molecule carries no net electrical charge. For amino acids and peptides, it is calculated as the average of the pKa values of the ionizable groups.
Henderson-Hasselbalch Equation: Used to calculate the pH of a solution when the ratio of conjugate base to acid is known:
Amino Acid Ionization: Amino acids have at least two ionizable groups: the amino group (pKa ~9-10) and the carboxyl group (pKa ~2-3). Some have additional ionizable side chains.