Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 27, Problem 27.49P
Following are a structural formula and a ball-and-stick model for the artificial sweetener aspartame. Each amino acid has the L configuration.
- (a) Name the two amino acids in this molecule.
- (b) Estimate the isoelectric point of aspartame.
- (c) Draw structural formulas for the products of hydrolysis of aspartame in 1 M HCl.
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Chapter 27 Solutions
Organic Chemistry
Ch. 27.1 - Of the 20 protein-derived amino acids shown in...Ch. 27.2 - Prob. 27.2PCh. 27.2 - Prob. 27.3PCh. 27.3 - Draw a structural formula for Lys-Phe-Ala. Label...Ch. 27.4 - Which of these tripeptides are hydrolyzed by...Ch. 27.4 - Deduce the amino acid sequence of an undecapeptide...Ch. 27.6 - Prob. 27.7PCh. 27 - What amino acid does each abbreviation stand for?...Ch. 27 - The configuration of the chiral center in -amino...Ch. 27 - Assign an R or S configuration to the chiral...
Ch. 27 - Prob. 27.11PCh. 27 - Prob. 27.12PCh. 27 - Draw zwitterion forms of these amino acids. (a)...Ch. 27 - Prob. 27.14PCh. 27 - Why is Arg often referred to as a basic amino...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Prob. 27.18PCh. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Both norepinephrine and epinephrine are...Ch. 27 - Prob. 27.22PCh. 27 - Draw a structural formula for the form of each...Ch. 27 - Prob. 27.24PCh. 27 - Write the zwitterion form of alanine and show its...Ch. 27 - Prob. 27.26PCh. 27 - Write the form of aspartic acid most prevalent at...Ch. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - For lysine and arginine, the isoelectric point,...Ch. 27 - Prob. 27.31PCh. 27 - Account for the fact that the isoelectric point of...Ch. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - At pH 7.4, the pH of blood plasma, do the majority...Ch. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - A chemically modified guanidino group is present...Ch. 27 - Draw a structural formula for the product formed...Ch. 27 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - A decapeptide has the following amino acid...Ch. 27 - Following is the primary structure of glucagon, a...Ch. 27 - Prob. 27.45PCh. 27 - Draw a structural formula of these tripeptides....Ch. 27 - Estimate the pI of each tripeptide in Problem...Ch. 27 - Glutathione (G-SH), one of the most common...Ch. 27 - Following are a structural formula and a...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - Prob. 27.52PCh. 27 - Prob. 27.53PCh. 27 - Prob. 27.54PCh. 27 - Distinguish between intermolecular and...Ch. 27 - Prob. 27.56PCh. 27 - Prob. 27.57P
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- Glutamic acid has three ionizable groups. The pKa of α-COOH is 2.19; a-NH 3+, 9.67; and the R-group, 4.25. What is the charge of glutamic acid at pH 10.00?arrow_forward(a) Draw the chemical structure of a generic amino acid,using R for the side chain. (b) When amino acids react toform proteins, do they do so via substitution, addition,or condensation reactions? (c) Draw the bond that linksamino acids together in proteins. What is this called?arrow_forward5arrow_forward
- 2. Classify the following amino acids as nonpolar, polar basic, polar acidic, or polar neutral. (a) (b) (c) (d) H₂N-CH-COH CH-OH I CH3 || H₂N-CH-C-OH I CH₂ C=O 1 OH H₂N-CH-C-OH CH₂ T CH-CH3 CH₂ H₂N-CH-C-OH ī CH₂ OH 229arrow_forward(a) Provide four distinct forms of phenylalanine. (b) Rank the solubility of these forms in water. (c) Explain your ranking.arrow_forwardGlutamic acid has three ionizable groups. The pKa of α-COOH is 2.19; α-NH 3 + , 9.67; and the R-group, 4.25. What is the predominant charge of glutamic acid at pH 10.00?arrow_forward
- Palmitoleic acid, a fatty acid with various pharmaceutical applications, is mainly obtained from macadamia nuts. The condensed structural formula for a triacylglycerol containing three palmitoleic acid units is provided below. Which of the following statements is NOT true regarding this triacylglycerol? O || CH,−O−C–(CH,)–CH=CH—(CH2)5–CH3 O || CH−O−C−(CH2)–CH=CH–(CH,)5–CH3 O CH,−O−C−(CH,)–CH=CH–(CH,)5–CH, O Its name is glyceryl tripalmitate or tripalmitin. O It is most likely to be liquid at room temperature. O It is an oil (not a fat). O It contains 3 molecules of the same unsaturated fatty acid.arrow_forwardProteins are polyamides formed from a-amino acids. Draw a partial structure of a protein by drawing three monomeric units of it.arrow_forwardQ1. The pKa values of Glutamic acid are 2.2, 4.3 and 9.7. H2N но. HO (a) Calculate the pH of a glutamic acid solution in which the a-amine group is 80% deprotonated? (show your calculation!) (b) Draw the ionic forms of glutamic acid that exist at the calculated pH.arrow_forward
- As a chef, you prepare a wide variety of foods daily. The following dishes all contain protein. What method (if any) has been used to denature the protein present in each food?(a) Charcoal-grilled steak(b) Pickled pigs’ feet(c) Meringue(d) Steak tartare (raw, chopped beef)(e) Salt porkarrow_forward(a) Why can’t two purine bases (A and G) form a base pair and hydrogen bond to each other on two strands of DNA in the double helix? (b) Why is hydrogen bonding between guanine and cytosine more favorable than hydrogen bonding between guanine and thymine?arrow_forward4r 19. Many lipids are found in the human body. One type of lipid is a triglyceride. Write the equation for the reaction between glycerol and stearic acid to form a triglyceride.arrow_forward
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