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Chapter 27: Problem 24

Draw a structural formula for the form of each amino most prevalent at pH \(10.0\). (a) Leucine (b) Valine (c) Proline (d) Aspartic acid

Short Answer

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Question: Draw the structural formulas of Leucine, Valine, Proline, and Aspartic acid at pH 10.0.

Step by step solution

01

a) Leucine

First, let's examine Leucine's structure. Leucine has the following chemical formula: H\(_2\)N-CH- (CH\(_2\)CH\(_2\)CH)\(_2\)(CH\(_3\))_2\(. As the given pH is 10.0, the amino group (NH\)_2\() will accept a proton and become charged as NH\)_3^+\(, and the carboxyl group (COOH) will lose a proton and become charged as COO\)^-\(. Thus, the structural formula for Leucine at pH 10.0 is: H\)_3\(N\)^+\(-CH- (CH\)_2\(CH\)_2\(CH)\)_2\((CH\)_3\()_2\) -COO^-$.
02

b) Valine

Valine's chemical formula is H\(_2\)N-CH-CH\(_3\)-(CH\(_3\))\(_2\)(CH\(_3\)). Similar to Leucine, the amino group will accept a proton due to the given pH of 10.0, resulting in the charged form NH\(_3^+\). The carboxyl group will lose a proton and become charged as COO\(^-\). The corresponding structural formula for Valine is: H\(_3\)N\(^+\)-CH-CH\(_3\)-(CH\(_3\))\(_2\)(CH\(_3\)) -COO^-$.
03

c) Proline

For Proline, the chemical formula is H\(_2\)N-CH-(CH\(_2\))\(_3\)-NH. Due to the pH of 10.0, the amino group will accept a proton, and the carboxyl group will lose a proton. Thus, Proline's structural formula becomes H\(_3\)N\(^+\)-CH-(CH\(_2\))\(_3\)-NH -COO^-$.
04

d) Aspartic acid

Aspartic acid's chemical formula is H\(_2\)N-CH-CH\(_2\)-COOH. In this case, the amino group will accept a proton, and the carboxyl group will lose a proton, similar to the other amino acids. However, the side chain also contains a carboxyl group (COOH). Since the given pH is 10.0, this side chain carboxyl group will also lose a proton. The resulting structural formula for Aspartic acid is: H\(_3\)N\(^+\)-CH-CH\(_2\)-COO\(^-\) -COO^-$. You now have the structural formulas for Leucine, Valine, Proline, and Aspartic acid at pH 10.0!

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Most popular questions from this chapter

Define the term zwitterion.

Do the following compounds migrate to the cathode or to the anode on electrophoresis at the specified pH? (a) Histidine at \(\mathrm{pH} 6.8\) (b) Lysine at \(\mathrm{pH} 6.8\) (c) Glutamic acid at \(\mathrm{pH} 4.0\) (d) Glutamine at pH \(4.0\) (e) Glu-Ile-Val at pH \(6.0\) (f) Lys-Gln-Tyr at \(p \mathrm{H} 6.0\)

For lysine and arginine, the isoelectric point, pI, occurs at a pH where the net charge on the nitrogen-containing groups is \(+1\) and balances the charge of \(-1\) on the \(\alpha\)-carboxyl group. Calculate pI for these amino acids.

Distinguish between intermolecular and intramolecular hydrogen bonding between the backbone groups on polypeptide chains. In what type of secondary structure do you find intermolecular hydrogen bonds? In what type do you find intramolecular hydrogen bonding?

At pH 7.4, with what amino acid side chains can the side chain of lysine form salt linkages?
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