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Problem 1 A. Aspartate has 3 pka values referring to its 3 readily (de)protonatable functional groups: 1.9, 3.6, and 9.6. Each pKa refers to the conjugate acid form of the functional group. Draw aspartate in this form, where each of the 3 functional groups is in its conjugate acid protonation state, labeling each functional group with the relevant pka. B. Briefly explain the rationale for your assignment of pka values above (max 2 sentences). C. Now draw aspartate in its most common protonation state at pH 7.6 (a common intracellular pH value).

Problem 1 A. Aspartate has 3 pka values referring to its 3 readily (de)protonatable functional groups: 1.9, 3.6, and 9.6. Each pKa refers to the conjugate acid form of the functional group. Draw aspartate in this form, where each of the 3 functional groups is in its conjugate acid protonation state, labeling each functional group with the relevant pka. B. Briefly explain the rationale for your assignment of pka values above (max 2 sentences). C. Now draw aspartate in its most common protonation state at pH 7.6 (a common intracellular pH value).

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Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1 A. Aspartate has 3 pka values referring to its 3 readily (de)protonatable functional groups: 1.9, 3.6, and 9.6. Each pka refers to the conjugate acid form of the functional group. Draw aspartate in this form, where each of the 3 functional groups is in its conjugate acid protonation state, labeling each functional group with the relevant pka. B. Briefly explain the rationale for your assignment of pka values above (max 2 sentences). C. Now draw aspartate in its most common protonation state at pH 7.6 (a common intracellular pH value). D. Redraw aspartate at its 2nd most common protonation state at pH 7.6. E. What is the approximate fraction of aspartate in each of these 2 protonation state at pH 7.6? F. To activate aspartate to react on its side chain, one option is to make the side chain into an acid chloride. Draw that analog. G. Draw the reaction of this analogue with diaminoethane (H2N-CH2-CH2-NH2), using the arrow formalism, clearly showing the major reaction intermediate. H. Mammalian metabolism does not involve acid chlorides. Draw two variants of aspartate that would be similarly activated to react (at the same position) with diaminoethane to produce the same nitrogen-containing product, but relying instead on functional groups found in central carbon metabolism. 1. The nitrogen-containing product of these reactions can undergo an intramolecular reaction to form a new C-N bond. Draw this reaction using the arrow formalism. J. Why is this reaction preferred over alternative intermolecular reaction(s) that could form the same functional group? (max one sentence)
Transcribed Image Text:Problem 1 A. Aspartate has 3 pka values referring to its 3 readily (de)protonatable functional groups: 1.9, 3.6, and 9.6. Each pka refers to the conjugate acid form of the functional group. Draw aspartate in this form, where each of the 3 functional groups is in its conjugate acid protonation state, labeling each functional group with the relevant pka. B. Briefly explain the rationale for your assignment of pka values above (max 2 sentences). C. Now draw aspartate in its most common protonation state at pH 7.6 (a common intracellular pH value). D. Redraw aspartate at its 2nd most common protonation state at pH 7.6. E. What is the approximate fraction of aspartate in each of these 2 protonation state at pH 7.6? F. To activate aspartate to react on its side chain, one option is to make the side chain into an acid chloride. Draw that analog. G. Draw the reaction of this analogue with diaminoethane (H2N-CH2-CH2-NH2), using the arrow formalism, clearly showing the major reaction intermediate. H. Mammalian metabolism does not involve acid chlorides. Draw two variants of aspartate that would be similarly activated to react (at the same position) with diaminoethane to produce the same nitrogen-containing product, but relying instead on functional groups found in central carbon metabolism. 1. The nitrogen-containing product of these reactions can undergo an intramolecular reaction to form a new C-N bond. Draw this reaction using the arrow formalism. J. Why is this reaction preferred over alternative intermolecular reaction(s) that could form the same functional group? (max one sentence)
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