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The enzyme dehydroquinate synthase catalyzes reactions (1) and (3) in the sequence shown

Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise ISBN: 9781936221349 461

Solution for problem 22.95 Chapter 22

Organic Chemistry | 6th Edition

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Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise

Organic Chemistry | 6th Edition

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Problem 22.95

The enzyme dehydroquinate synthase catalyzes reactions (1) and (3) in the sequence shown in Fig. P22.97 on p. 1182, which is part of the pathway for the biosynthesis of aromatic amino acids such as tryptophan; reactions (2), (4), and (5) occur spontaneously. (a) Assuming that acids and bases are present as needed, propose a curved-arrow mechanism for reaction (2). To what laboratory reaction is this reaction analogous? [Hint: Phosphate is a leaving group in reaction (2).] (b) The two enzyme-catalyzed steps (1) and (3) are, respectively, an oxidation and a reduction that consume and then regenerate an NAD+ and result in no net change at the carbon involved. What is the chemical rationale for these two reactions? [Hint: Why is reaction (1) necessary for the success of reaction (2)?] (c) Assuming that acids and bases are present as needed, propose curved-arrow mechanisms for reactions (4) and (5). To what laboratory reactions are these similar?

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Textbook: Organic Chemistry
Edition: 6
Author: Marc Loudon, Jim Parise
ISBN: 9781936221349

Since the solution to 22.95 from 22 chapter was answered, more than 228 students have viewed the full step-by-step answer. The full step-by-step solution to problem: 22.95 from chapter: 22 was answered by , our top Chemistry solution expert on 03/16/18, 03:35PM. The answer to “The enzyme dehydroquinate synthase catalyzes reactions (1) and (3) in the sequence shown in Fig. P22.97 on p. 1182, which is part of the pathway for the biosynthesis of aromatic amino acids such as tryptophan; reactions (2), (4), and (5) occur spontaneously. (a) Assuming that acids and bases are present as needed, propose a curved-arrow mechanism for reaction (2). To what laboratory reaction is this reaction analogous? [Hint: Phosphate is a leaving group in reaction (2).] (b) The two enzyme-catalyzed steps (1) and (3) are, respectively, an oxidation and a reduction that consume and then regenerate an NAD+ and result in no net change at the carbon involved. What is the chemical rationale for these two reactions? [Hint: Why is reaction (1) necessary for the success of reaction (2)?] (c) Assuming that acids and bases are present as needed, propose curved-arrow mechanisms for reactions (4) and (5). To what laboratory reactions are these similar?” is broken down into a number of easy to follow steps, and 154 words. Organic Chemistry was written by and is associated to the ISBN: 9781936221349. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 6. This full solution covers the following key subjects: . This expansive textbook survival guide covers 239 chapters, and 1693 solutions.

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The enzyme dehydroquinate synthase catalyzes reactions (1) and (3) in the sequence shown