Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 24.6, Problem 24.13P
Suggest how you would separate the free i-ammo acid from its acylated D enantiomer in Figure24-5.
Figure 24-5
Selective enzymatic deacylation. An acylase enzyme (such as hog kidney acylase or carboxypeptidase) deacylates only the natural L-amino acid.
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In 1891, Emil Fischer determined the structures of glucose and the seven other d-aldohexoses using only simple chemical reactions and clever reasoning about stereochemistry andsymmetry. He received the Nobel Prize for this work in 1902. Fischer had determined thatd-glucose is an aldohexose, and he used Ruff degradations to degrade it to (+)-glyceraldehyde. Therefore, the eight d-aldohexose structures shown in Figure 23-3 are the possiblestructures for glucose.Pretend that no names are shown in Figure 23-3 except for glyceraldehyde, and usethe following results to prove which of these structures represent glucose, mannose,arabinose, and erythrose.(a) Upon Ruff degradation, glucose and mannose give the same aldopentose: arabinose.Nitric acid oxidation of arabinose gives an optically active aldaric acid. What are thetwo possible structures of arabinose?(b) Upon Ruff degradation, arabinose gives the aldotetrose erythrose. Nitric acid oxidation of erythrose gives an optically inactive…
In 1891, Emil Fischer determined the structures of glucose and the seven other d-aldohexoses using only simple chemical reactions and clever reasoning about stereochemistry andsymmetry. He received the Nobel Prize for this work in 1902. Fischer had determined thatd-glucose is an aldohexose, and he used Ruff degradations to degrade it to (+)-glyceraldehyde. Therefore, the eight d-aldohexose structures shown in Figure 23-3 are the possiblestructures for glucose.Pretend that no names are shown in Figure 23-3 except for glyceraldehyde, and usethe following results to prove which of these structures represent glucose, mannose,arabinose, and erythrose.(a) Upon Ruff degradation, glucose and mannose give the same aldopentose: arabinose.Nitric acid oxidation of arabinose gives an optically active aldaric acid. What are thetwo possible structures of arabinose?(b) Upon Ruff degradation, arabinose gives the aldotetrose erythrose. Nitric acid oxidation of erythrose gives an optically inactive…
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Chapter 24 Solutions
Organic Chemistry (9th Edition)
Ch. 24.2A - Draw three-dimensional representations of the...Ch. 24.2A - Prob. 24.2PCh. 24.2B - The herbicide glyphosate (Roundup) kills plants by...Ch. 24.4 - Draw the structure of the predominant form of a....Ch. 24.4 - Draw the resonance forms of a protonated guanidino...Ch. 24.4 - Although tryptophan contains a heterocyclic amine,...Ch. 24.4 - Prob. 24.7PCh. 24.4 - Prob. 24.8PCh. 24.5A - Show how the following amino acids might be formed...Ch. 24.5B - Prob. 24.10P
Ch. 24.5C - Prob. 24.11PCh. 24.5C - Show how you would use a Strecker synthesis to...Ch. 24.6 - Suggest how you would separate the free i-ammo...Ch. 24.7A - Propose a mechanism for the acid-catalyzed...Ch. 24.7A - Give equations for the formation and...Ch. 24.7B - Prob. 24.16PCh. 24.7C - Prob. 24.17PCh. 24.8B - Draw the complete structures of the following...Ch. 24.9C - Prob. 24.19PCh. 24.9C - Prob. 24.20PCh. 24.9C - Prob. 24.21PCh. 24.9E - Prob. 24.22PCh. 24.9E - Prob. 24.23PCh. 24.10A - Propose a mechanism for the coupling of acetic...Ch. 24.10B - Show how you would synthesize Leu-Gly-Ala-Val-Phe...Ch. 24.10B - Show how solid-phase peptide synthesis would be...Ch. 24 - a. The isoelectric point (pl) of phenylalanine is...Ch. 24 - Prob. 24.28SPCh. 24 - Prob. 24.29SPCh. 24 - Prob. 24.30SPCh. 24 - Prob. 24.31SPCh. 24 - Suggest a method for the synthesis of the...Ch. 24 - Prob. 24.33SPCh. 24 - Write the complete structures for the following...Ch. 24 - The following structure is drawn in an...Ch. 24 - Prob. 24.36SPCh. 24 - Prob. 24.37SPCh. 24 - Show the steps and intermediates in the synthesis...Ch. 24 - Prob. 24.39SPCh. 24 - Lipoic acid is often found near the active sites...Ch. 24 - Prob. 24.41SPCh. 24 - Prob. 24.42SPCh. 24 - Prob. 24.43SPCh. 24 - Complete hydrolysis of an unknown basic...Ch. 24 - Prob. 24.45SPCh. 24 - Prob. 24.46SPCh. 24 - Prob. 24.47SP
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