a) Canavanine is an amino acid that is produced by some legume plants. It is not used in proteins but serves as a nitrogen storage molecule in seeds, and is being investigated as a possible anti-cancer and anti-viral drug. Canavanine's amino and carboxyl groups are the same as those in any other amino acid (pKa for the amino group is 8.0 and pKa for the carboxyl group is 3.1), and its side group has a single ionizable group with a pKa of 7.0. Describe or explain what that statement (the previous sentence) tells you about the protonation state of each of the 3 ionizable groups on this amino acid if it is dissolved in pure distilled water at pH 7.0.

Chemistry & Chemical Reactivity
9th Edition
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Chapter24: Biochemistry
Section24.1: Proteins
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 4a) Canavanine is an amino acid that is produced by some legume plants. It is not used in
proteins but serves as a nitrogen storage molecule in seeds, and is being investigated as a
possible anti-cancer and anti-viral drug. Canavanine's amino and carboxyl groups are the same as
those in any other amino acid (pKa for the amino group is 8.0 and pKa for the carboxyl group is
3.1), and its side group has a single ionizable group with a
pKa of 7.0. Describe or explain what that statement (the previous sentence) tells you about the
protonation state of each of the 3 ionizable groups on this amino acid if it is dissolved in pure
distilled water at pH 7.0. 

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