Question

1. Examine the peptide below and determine the net charge at (a) pH 2 and, (b) pH 8.5. [6 marks) Cys— Phe-Ile — Glu — Asn — C can you help me with this question please
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Answer #1

Take the pKa value from table and consider only the amino group of first amino acid, side chain groups and carboxylic group of last amino acid. All the amino and carboxylic group in the middle are part of peptide bond. So they can't influence charge

Charge at pH 2

Cys has +1 charge at amino group

Phe, Asn, Glu and Ile are neutral (Phe, Asn, Ile doesn't have any charge side chain group)

Cys, Pro, and Gly are neutral

His has +1 charge

So the net chare on peptide is +2

Charge at pH 8.5

Cystein side chain has SH that does participate in charge distribution. Amino group of cystein has pKa around 10 and will not give proton at pH 8.5. So cystein would have +1 charge.

Phe, Iso are neutral

Glu has -1 charge due deprotonated carboxylic group

Asn, Pro, Cys, and His would be neutral

Gly has -1 charge due to deprotonated carboxylic group.

So net charge would be -1.

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