Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 24.4, Problem 24.6P
Although tryptophan contains a heterocyclic
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Although tryptophan contains a heterocyclic amine, it is considered a neutral aminoacid. Explain why the indole nitrogen of tryptophan is more weakly basic than one ofthe imidazole nitrogens of histidine.
α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis.
What aldehyde is needed to prepare isoleucine?
Another method to form a peptide bond involves a two-step process
Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.
Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?
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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- Draw the structure of alanine in a solution at pH = 0arrow_forwardExplain why the ability of PLP to catalyze an amino acid transformation is greatly reduced if a PLP-requiring enzymatic reaction is carried out at a pH at which the pyridine nitrogen is not protonated.arrow_forwardDraw the structure for each of the following peptides in their fully protonated forms. Indicate which protons are dissociable in the structure. a) Gly-Lys-Arg-Phe b) Y-D-S-C-Qarrow_forward
- Another method to form a peptide bond involves a two-step process Reaction of the p-nitrophenyl ester with an amino acid ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forwardAt very low pH, alanine is a diprotic acid that can be represented as H3N1-CH(CH3)-COOH. The pKa of the carboxyl group is 2.3, and the pKa of the UNH1 3 group is 9.7.(a) At pH 7, what fraction of the amino acid molecules dissolved in an aqueous solution will have the form H3N1-CH(CH3)-COO2?(b) What fraction of the molecules at this pH will havethe form H2N-CH(CH3)-COOH?arrow_forwardAnother method to form a peptide bond involves a two-step process:[1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.[2] Reaction of the p-nitrophenyl ester with an amino acid ester.a. Why does a p-nitrophenyl ester “activate” the carboxy group of the first amino acid to amide formation? b. Would a p-methoxyphenyl ester perform the same function? Why or why not?arrow_forward
- Pentapeptide has a sequence of APEDS Structure of pentapeptide in its proper ionization state at pH 7.0 what is the pI of pentapeptide?arrow_forwardIf a heptapeptide is made of Y-P-G-P-H-I-L amino acid sequence, what qualitative tests will give positive results when it is subjected to acid hydrolysis?arrow_forwardOriginally the amino acid itself was considered to be used as a flavor enhancer, but MSG was determined to have better water solubility. Why is that the case?arrow_forward
- Draw the synthesis scheme of the Alanine-Leucine dipeptide. In the synthesis, the tert-butoxycarbonyl protecting groups and the benzyl ester must be used, in addition to the formation of the peptide bond driven by dicyclohexylcarbodiimide.arrow_forwardWhat type of interaction (IMF) would be present between side chains of the following amino acid residues? Explain your answers. a) 2 phenylalanine residues b) Methionine and valine residues c) Glutamate and arginine residuesarrow_forwardShow how valine can be prepared by a reductive amination.arrow_forward
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