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Question

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)4NH2
V CH2CONH2 CH2CONH2
VI (CH2)4NH2 (CH2)4NH2
VII CH2COOH CH2CONH2
VIII CH2OH (CH2)4NH2
IX (CH2)4NH2 CH3

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Solution

In the given general structure of amino acid we have R1 and R2 group.
At pH- 7, the carboxylic acid will exist in carboxylate form since it is a strong acid. So for make the amino acid positively charge it should have more than one strong basic group. Thus, these basic group will get protonated at pH-7 and they becomes positively charge.
Hence, among R1 and R2 atleat one should be have a strong basic group to get positively charged peptide.
Amide are less basic than amine because their lone pair involved in resonance. Amine are basic enough to get protonated at pH-7
Hence, peptide (IV), (VI), (VIII) and (IX) are positively charged at pH-7.

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