Mechanism Problems -

PROBLEM The reaction of ninhydrin with an $\alpha$-amino acid occurs in several steps.
26-24 (a) The first step is formation of an imine by reaction of the amino acid with ninhydrin. Show its structure and the mechanism of its formation.
(b) The second step is a decarboxylation. Show the structure of the product and the mechanism of the decarboxylation reaction.
(c) The third step is hydrolysis of an imine to yield an amine and an aldehyde. Show the structures of both products and the mechanism of the hydrolysis reaction.
(d) The final step is formation of the purple anion. Show the mechanism of the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0971.jpg?height=248&width=1419&top_left_y=1600&top_left_x=475)


Mechanism Problems -

Ninhydrin
PROBLEM The chloromethylated polystyrene resin originally used for Merrifield solid-phase peptide
26-25 synthesis was prepared by treatment of polystyrene with chloromethyl methyl ether and a Lewis acid catalyst. Propose a mechanism for the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0971.jpg?height=286&width=695&top_left_y=2074&top_left_x=411)


Mechanism Problems -

PROBLEM An Fmoc protecting group can be removed from an amino acid by treatment with the amine base 26-26 piperidine. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0972.jpg?height=310&width=1359&top_left_y=189&top_left_x=413)


Mechanism Problems -

Fmoc-protected amino acid


Mechanism Problems -

PROBLEM Proteins can be cleaved specifically at the amide bond on the carboxyl side of methionine residues 26-27 by reaction with cyanogen bromide, $\mathrm{BrC} \equiv \mathrm{N}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0972.jpg?height=219&width=1251&top_left_y=733&top_left_x=418)


Mechanism Problems -

The reaction occurs in several steps:
(a) The first step is a nucleophilic substitution reaction of the sulfur on the methionine side chain with BrCN to give a cyanosulfonium ion, $\left[\mathrm{R}_{2} \mathrm{SCN}\right]^{+}$. Show the structure of the product, and propose a mechanism for the reaction.
(b) The second step is an internal $\mathrm{S}_{\mathrm{N}} 2$ reaction, with the carbonyl oxygen of the methionine residue displacing the positively charged sulfur leaving group and forming a five-membered ring product. Show the structure of the product and the mechanism of its formation.
(c) The third step is a hydrolysis reaction to split the peptide chain. The carboxyl group of the former methionine residue is now part of a lactone (cyclic ester) ring. Show the structure of the lactone product and the mechanism of its formation.
(d) The final step is a hydrolysis of the lactone to give the product shown. Show the mechanism of the reaction.


Mechanism Problems -

PROBLEM A clever recent method of peptide synthesis involves formation of an amide bond by reaction of an
26-28 $\alpha$-keto acid with an $N$-alkylhydroxylamine:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0972.jpg?height=177&width=1042&top_left_y=1733&top_left_x=430)


Mechanism Problems -

An $\boldsymbol{\alpha}$-keto acid $\quad$ A hydroxylamine $\quad$ An amide
The reaction is thought to occur by nucleophilic addition of the $N$-alkylhydroxylamine to the keto acid as if forming an oxime (Section 19.8), followed by decarboxylation and elimination of water. Show the mechanism.


Amino Acid Structures and Chirality -

PROBLEM Except for cysteine, only $S$ amino acids occur in proteins. Several $R$ amino acids are also found in 26-29 nature, however. ( $R$ )-Serine is found in earthworms, and ( $R$ )-alanine is found in insect larvae. Draw Fischer projections of $(R)$-serine and $(R)$-alanine. Are these D or L amino acids?


Amino Acid Structures and Chirality -

PROBLEM Cysteine is the only amino acid that has L stereochemistry but an $R$ configuration. Make up a 26-30 structure for another $L$ amino acid of your own creation that also has an $R$ configuration.


Amino Acid Structures and Chirality -

PROBLEM Draw a Fischer projection of ( $S$ ) -proline. 26-31


Amino Acid Structures and Chirality -

PROBLEM Show the structures of the following amino acids in their zwitterionic forms:
26-32 (a) $\operatorname{Trp}$
(b) Ile
(c) Cys
(d) His


Amino Acid Structures and Chirality -

PROBLEM Proline has $\mathrm{p} K_{\mathrm{a} 1}=1.99$ and $\mathrm{p} K_{\mathrm{a} 2}=10.60$. Use the Henderson-Hasselbalch equation to calculate the
26-33 ratio of protonated and neutral forms at $\mathrm{pH}=2.50$. Calculate the ratio of neutral and deprotonated forms at $\mathrm{pH}=9.70$.


Amino Acid Structures and Chirality -

PROBLEM Using both three- and one-letter codes for amino acids, write the structures of all possible peptides
26-34 that contain the following amino acids:
(a) Val, Ser, Leu
(b) $\mathrm{Ser}, \mathrm{Leu}_{2}$, Pro


Amino Acid Structures and Chirality -

PROBLEM Look at the side chains of the 20 amino acids in Table 26.1, and then think about what is not 26-35 present. None of the 20 contain either an aldehyde or a ketone carbonyl group, for instance. Is this just one of nature's oversights, or is there a likely chemical reason? What complications might an aldehyde or ketone carbonyl group cause?


Amino Acid Synthesis and Reactions -

PROBLEM Show how you could use the acetamidomalonate method to prepare the following amino acids:
26-36 (a) Leucine (b) Tryptophan
PROBLEM Show how you could prepare the following amino acids using a reductive amination:
26-37 (a) Methionine (b) Isoleucine
PROBLEM Show how you could prepare the following amino acids enantioselectively:
26-38 (a) Pro (b) Val
PROBLEM Serine can be synthesized by a simple variation of the amidomalonate method using formaldehyde 26-39 rather than an alkyl halide. How might this be done?


Amino Acid Synthesis and Reactions -

PROBLEM Predict the product of the reaction of valine with the following reagents:
26-40 (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$, acid (b) Di-tert-butyl dicarbonate (c) $\mathrm{KOH}, \mathrm{H}_{2} \mathrm{O}$
(d) $\mathrm{CH}_{3} \mathrm{COCl}$, pyridine; then $\mathrm{H}_{2} \mathrm{O}$


Amino Acid Synthesis and Reactions -

PROBLEM Draw resonance forms for the purple anion obtained by reaction of ninhydrin with an $\alpha$-amino acid 26-41 (see Problem 26-24).


Peptides and Enzymes -

PROBLEM Write full structures for the following peptides:
26-42 (a) C-H-E-M (b) P-E-P-T-I-D-E


Peptides and Enzymes -

PROBLEM Propose two structures for a tripeptide that gives Leu, Ala, and Phe on hydrolysis but does not react 26-43 with phenyl isothiocyanate.


Peptides and Enzymes -

PROBLEM Show the steps involved in a synthesis of Phe-Ala-Val using the Merrifield procedure. 26-44


Peptides and Enzymes -

PROBLEM Draw the structure of the PTH derivative product you would obtain by Edman degradation of the 26-45 following peptides:
(a) I-L-P-F (b) D-T-S-G-A


Peptides and Enzymes -

PROBLEM Which amide bonds in the following polypeptide are cleaved by trypsin? By chymotrypsin?
26-46
Phe-Leu-Met-Lys-Tyr-Asp-Gly-Gly-Arg-Val-Ile-Pro-Tyr
PROBLEM What kinds of reactions do the following classes of enzymes catalyze?
26-47 (a) Hydrolases (b) Lyases (c) Transferases


Peptides and Enzymes -

PROBLEM Which of the following amino acids are more likely to be found on the exterior of a globular protein, 26-48 and which on the interior? Explain.
(a) Valine
(b) Aspartic acid
(c) Phenylalanine
(d) Lysine


Peptides and Enzymes -

PROBLEM Leuprolide is a synthetic nonapeptide used to treat both endometriosis in women and prostate 26-49 cancer in men.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0974.jpg?height=616&width=1429&top_left_y=456&top_left_x=413)
(a) Both C-terminal and N -terminal amino acids in leuprolide have been structurally modified. Identify the modifications.
(b) One of the nine amino acids in leuprolide has D stereochemistry rather than the usual L. Which one?
(c) Write the structure of leuprolide using both one- and three-letter abbreviations.
(d) What charge would you expect leuprolide to have at neutral pH ?


General Problems -

PROBLEM The $\alpha$-helical parts of myoglobin and other proteins stop whenever a proline residue is encountered
26-50 in the chain. Why is proline never present in a protein $\alpha$ helix?
PROBLEM Arginine, the most basic of the 20 common amino acids, contains a guanidino functional group in
26-51 its side chain. Explain, using resonance structures to show how the protonated guanidino group is stabilized.
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General Problems -

Arginine


General Problems -

PROBLEM Cytochrome $c$ is an enzyme found in the cells of all aerobic organisms. Elemental analysis of 26-52 cytochrome $c$ shows that it contains $0.43 \%$ iron. What is the minimum molecular weight of this enzyme?


General Problems -

PROBLEM Evidence for restricted rotation around amide $\mathrm{O}=\mathrm{C}-\mathrm{N}$ bonds comes from NMR studies. At room 26-53 temperature, the ${ }^{1} \mathrm{H}$ NMR spectrum of $\mathrm{N}, \mathrm{N}$-dimethylformamide shows three peaks: $2.9 \mathrm{\delta}$ (singlet, 3 H ), $3.0 \mathrm{\delta}$ (singlet, 3 H ), and $8.0 \delta$ (singlet, 1 H ). As the temperature is raised, however, the two singlets at $2.9 \delta$ and $3.0 \delta$ slowly merge. At $180^{\circ} \mathrm{C}$, the ${ }^{1} \mathrm{H}$ NMR spectrum shows only two peaks: $2.95 \delta$ (singlet, 6 H ) and $8.0 \delta$ (singlet, 1 H ). Explain this temperature-dependent behavior.


General Problems -

PROBLEM Propose a structure for an octapeptide that shows the composition Asp, Gly $y_{2}$, Leu, Phe, $\mathrm{Pro}_{2}$, Val 26-54 on amino acid analysis. Edman analysis shows a glycine N-terminal group, and leucine is the C-
terminal group. Acidic hydrolysis gives the following fragments:
Val-Pro-Leu, Gly, Gly-Asp-Phe-Pro, Phe-Pro-Val
PROBLEM Look at the structure of human insulin, and indicate where in each chain the molecule is cleaved by 26-55 trypsin and chymotrypsin.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0975.jpg?height=497&width=1210&top_left_y=451&top_left_x=417)


Insulin -

PROBLEM What is the structure of a nonapeptide that gives the following fragments when cleaved?
26-56
Trypsin cleavage: Val-Val-Pro-Tyr-Leu-Arg, Ser-Ile-Arg
Chymotrypsin cleavage: Leu-Arg, Ser-Ile-Arg-Val-Val-Pro-Tyr


Insulin -

PROBLEM Oxytocin, a nonapeptide hormone secreted by the pituitary gland, functions by stimulating uterine
26-57 contraction and lactation during childbirth. Its sequence was determined from the following evidence:


Insulin -

1. Oxytocin is a cyclic compound containing a disulfide bridge between two cysteine residues.
2. When the disulfide bridge is reduced, oxytocin has the constitution Asn, Cys ${ }_{2}$, Gln, Gly, Ile, Leu, Pro, Tyr.
3. Partial hydrolysis of reduced oxytocin yields seven fragments: Asp-Cys, Ile-Glu, Cys-Tyr, Leu-Gly, Tyr-Ile-Glu, Glu-Asp-Cys, and Cys-Pro-Leu.
4. Gly is the C-terminal group.
5. Both Glu and Asp are present as their side-chain amides (Gln and Asn) rather than as free sidechain acids.


Insulin -

What is the amino acid sequence of reduced oxytocin? What is the structure of oxytocin itself?


Insulin -

PROBLEM Aspartame, a nonnutritive sweetener marketed under such trade names as Equal, NutraSweet, and 26-58 Canderel, is the methyl ester of a simple dipeptide, Asp-Phe-OCH3.
(a) Draw the structure of aspartame.
(b) The isoelectric point of aspartame is 5.9. Draw the principal structure present in aqueous solution at this pH .
(c) Draw the principal form of aspartame present at physiological $\mathrm{pH}=7.3$.


Insulin -

PROBLEM Refer to Figure 26.5 and propose a mechanism for the final step in Edman degradation-the acid-
26-59 catalyzed rearrangement of the ATZ derivative to the PTH derivative.
PROBLEM Amino acids are metabolized by a transamination reaction in which the $-\mathrm{NH}_{2}$ group of the amino
26-60 acid changes places with the keto group of an $\alpha$-keto acid. The products are a new amino acid and a new $\alpha$-keto acid. Show the product from transamination of isoleucine.


Insulin -

PROBLEM The first step in the biological degradation of histidine is formation of a 26-61 4-methylidene-5-imidazolone (MIO) by cyclization of a segment of the peptide chain in the histidine ammonia lyase enzyme. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0976.jpg?height=301&width=911&top_left_y=346&top_left_x=409)


Insulin -

4-Methylidene-5-imidazolone (MIO)
PROBLEM The first step in the biological degradation of lysine is reductive amination with $\alpha$-ketoglutarate to
26-62 give saccharopine. Nicotinamide adenine dinucleotide phosphate (NADPH), a relative of NADH, is the reducing agent. Show the mechanism.
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Lysine
$+$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0976.jpg?height=109&width=225&top_left_y=1016&top_left_x=847)
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$\alpha$-Ketoglutarate


CHAPTER 27 -

Biomolecules: Lipids
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0977.jpg?height=1021&width=1890&top_left_y=346&top_left_x=231)


CHAPTER 27 -

FIGURE 27.1 Soap bubbles, so common yet so beautiful, are made from animal fat, a lipid. (credit: "Reflections in soap bubbles" by Image Picture Photography/Flickr, CC BY 2.0)


CHAPTER CONTENTS -


CHAPTER CONTENTS - 27.1 Waxes, Fats, and Oils

27.2 Soap
27.3 Phospholipids
27.4 Prostaglandins and Other Eicosanoids
27.5 Terpenoids
27.6 Steroids
27.7 Biosynthesis of Steroids


WHY THIS CHAPTER? We've now covered two of the four major classes of biomolecules-proteins and carbohydrates-and have two remaining. In this chapter, we'll cover lipids, the largest and most diverse class of biomolecules, looking both at their structure and function and at their metabolism.


Lipids are naturally occurring organic molecules that have limited solubility in water and can be isolated from organisms by extraction with nonpolar organic solvents. Fats, oils, waxes, many vitamins and hormones, and most nonprotein cell-membrane components are some examples. Note that this definition differs from the sort used for carbohydrates and proteins in that lipids are defined by a physical property (solubility) rather than by structure. Of the many kinds of lipids, we'll be concerned in this chapter with only a few: triacylglycerols, eicosanoids, terpenoids, and steroids.