Chemistry 3.13- Amino Acids, Proteins and DNA

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What are zwitterions?

  • Since amino acids contain a basic amino group and an acidic carboxyl group, an intramolecular neutralisation reaction occurs

  • This forms a zwitterion, which has both a positive (NH3+) and negative (COO-) charge

<ul><li><p>Since amino acids contain a basic amino group and an acidic carboxyl group, an<strong> intra</strong>molecular neutralisation reaction occurs </p></li><li><p>This forms a zwitterion, which has both a <strong>positive </strong><span>(NH</span><sub>3</sub><sup>+</sup><span>) and </span><strong>negative </strong><span>(COO</span><sup>-</sup><span>) charge</span></p></li></ul><p></p>
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How do amino acids exist at different pHs?

  • At a low pH, the presence of H+ ions will reprotonate the COO- group in the zwitterion (reforming the COOH), so the amino acid will exist as a cation

  • At a high pH, the presence of OH- ions will deprotonate the NH3+ group in the zwitterion (reforming the NH2), so the amino acid will exist as an anion

<ul><li><p>At a <strong>low pH</strong>, the presence of <strong>H<sup>+</sup></strong><sup> </sup>ions will <strong>reprotonate </strong>the <strong>COO<sup>-</sup> </strong>group in the <strong>zwitterion</strong> (reforming the <strong>COOH</strong>), so the amino acid will exist as a <strong>cation</strong></p></li><li><p>At a <strong>high</strong> <strong>pH</strong>, the presence of <strong>OH<sup>- </sup></strong>ions will <strong>deprotonate </strong>the <strong>NH<sub>3</sub><sup>+</sup> </strong>group in the <strong>zwitterion </strong>(reforming the <strong>NH<sub>2</sub></strong>), so the amino acid will exist as an <strong>anion</strong></p></li></ul><p></p>
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