A peptide has the sequence   Glu–His–Trp–Ser–Gly–Leu–Arg–Pro–GlyGlu–His–Trp–Ser–Gly–Leu–Arg–Pro–Gly   The p?a values for the peptide’s side chains, terminal amino groups, and carboxyl groups are provided in the table. Amino acid Amino pKa Carboxyl pKa Side‑chain pKa glutamate 9.609.60 2.342.34 4.254.25 histidine 9.179.17 1.821.82 6.006.00 tryptophan 9.399.39 2.382.38   serine 9.159.15 2.212.21   glycine 9.609.60 2.342.34   leucine 9.609.60 2.362.36   arginine 9.049.04 2.172.17 12.4812.48 proline 10.9610.96 1.991.99

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter26: Biomolecules: Amino Acids, Peptides, And Proteins
Section26.SE: Something Extra
Problem 34AP: Using both three- and one-letter codes for amino acids, write the structures of all possible...
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A peptide has the sequence

 

Glu–His–Trp–Ser–Gly–Leu–Arg–Pro–GlyGlu–His–Trp–Ser–Gly–Leu–Arg–Pro–Gly

 

The p?a values for the peptide’s side chains, terminal amino groups, and carboxyl groups are provided in the table.

Amino acid Amino pKa Carboxyl pKa Side‑chain pKa
glutamate 9.609.60 2.342.34 4.254.25
histidine 9.179.17 1.821.82 6.006.00
tryptophan 9.399.39 2.382.38  
serine 9.159.15 2.212.21  
glycine 9.609.60 2.342.34  
leucine 9.609.60 2.362.36  
arginine 9.049.04 2.172.17 12.4812.48
proline 10.9610.96 1.991.99  
 
 
Calculate the net charge of the molecule at pH 8
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