Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 22.9, Problem 17P
Carboxypeptidase A has esterase activity as well as peptidase activity, so it can hydrolyze ester bonds as well as peptide bonds. When carboxypeptidase A hydrolyzes ester bonds. Glu 270 acts as a nucleophilic catalyst instead of a general-base catalyst. Propose a mechanism for the carboxypeptidase A-catalyzed hydrolysis of an ester bond.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Gramicidin S, a topical antibiotic produced by the bacterium Bacillus brevis, is a cyclic decapeptide formed from five amino acids. Draw the structures of the amino acids that form gramicidin S, and explain why this compound possesses two unusual structural features.
Choose among these options
Among these Inhibits the enzyme which is responsible for the assembly of matured viral particles
Saquinavir
Didanosine
Penciclovir
Azidothymidine
The following are essential components in the structure of sulfonamides with the exception of
Amino group
Benzene ring
Pyridine
N-Acyl amino
This drug has been associated with optic neuritis and therefore discontinued after 2 months of treatment
Isonizaid
Rifampicin
Ethambutol
Pyrazinamide
A non prodrug ACE Inhibitor
Captopril
Enalapril
Quinapril
Fosinopril
High sodium diet
High fat diet
Low potassium diet
Low phosphate diet
Which of the following substituent is an ortho/para-directing activator and an ortho/para-directing deactivator?
a
amino group
b
halogen group
c
nitro group
d
carboxyl group
Chapter 22 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 22.2 - Compare each of the mechanisms listed here with...Ch. 22.2 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.3 - a. Draw the mechanism for the following reaction...Ch. 22.5 - Prob. 7PCh. 22.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 22.6 - Prob. 9PCh. 22.7 - Prob. 10PCh. 22.7 - Prob. 12PCh. 22.7 - Prob. 13P
Ch. 22.9 - Which of the following amino acid side chains can...Ch. 22.9 - Which of the following C-terminal peptide bonds is...Ch. 22.9 - Carboxypeptidase A has esterase activity as well...Ch. 22.10 - Arginine and lysine side chains fit into trypsins...Ch. 22.10 - Explain why serine proteases do not catalyze...Ch. 22.11 - If H2 18O is used in the hydrolysis reaction...Ch. 22.11 - Draw the pH-activity profile for an enzyme that...Ch. 22.12 - The pHactivity profile for glucose-6-phosphate...Ch. 22.12 - Prob. 23PCh. 22.13 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 22.13 - What advantage does the enzyme gain by forming an...Ch. 22.13 - Prob. 26PCh. 22.13 - Prob. 27PCh. 22.13 - Aldolase shows no activity if it is incubated with...Ch. 22 - Which of the following parameters would be...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Indicate the type of catalysis that is occurring...Ch. 22 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 22 - Prob. 34PCh. 22 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 22 - there are two kinds of aldolases. Class I...Ch. 22 - Prob. 37PCh. 22 - The hydrolysis of the ester shown here is...Ch. 22 - Prob. 39PCh. 22 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 22 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 22 - Proof that an imine was formed between aldolase...Ch. 22 - Prob. 43PCh. 22 - a. Explain why the alkyl halide shown here reacts...Ch. 22 - Triosephosphate isomerase (TIM) catalyzes the...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Use curved arrows to illustrate how the following decarboxylation occurs in the presence of an acid HA. This reaction constitutes one step in the biosynthesis of the amino acid tyrosine.arrow_forwardα-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?arrow_forwardThe following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph Ph `N' `N' ČH3 ČH3 Methsuximide Ethosuximide Phensuximide Following is a synthesis of phensuximide. CN Ph CN Ph CN 1. NaOH, H2O 2. HC, Н20 NaOEt KCN Ph-CHO cOOEt H cOOEt NC COOEt 3. Нeat Ethyl cyanoacetate (A) (B) Benzaldehyde Ph Ph Ph CH;NH2 НООС СООН Et0oC COOEt `N' (C) (D) ČH3 Phensuximide Methsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis of methsuximide.arrow_forward
- A chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.arrow_forwardSeveral compounds have been found to inhibit -lactamase, and drugs based on these compounds can be taken in combination with penicillins and cephalosporins to restore their effectiveness when resistance is known to be a problem. The commonly prescribed formulation called Augmentin is a combination of the -lactamase inhibitor shown below with amoxicillin (shown above). It is used to treat childhood ear infections when resistance is suspected, and many kids know it as the white liquid that tastes like bananas. Which of the statements below are true statements? 1. The stereochemistry of the fusion between the four-and five-membered rings in the inhibitor and amoxicillin are different. 2. The inhibitor possesses enol ether and allylic alcohol functional groups while the antibiotic possesses a phenol and a secondary amide functional group. 3. Neither the inhibitor nor the antibiotic contains strained rings. 4. Both 1 and 2 are true.arrow_forwardA variation of the acetamidomalonate synthesis can be used to synthesize serine. The process involves the following steps: Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1; Enolate anion 1 makes a nucleophilic attack on formaldehyde, forming tetrahedral intermediate 2; Protonation of the oxyanion forms alcohol 3; Acid hydrolysis yields dicarboxyamino alcohol 4; Decarboxylation leads to the final amino acid. Write out the mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 2. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. Draw carboxyl and amino groups in their uncharged forms.arrow_forward
- но- OH + HO-CH3 но -CH3 + H20 phosphoric acid methanol methyl phosphate water Formation of a phosphate ester Assuming phosphoric acid undergoes a similar reaction to that of carboxylic acids, outline a mechanism for the formation of methylphosphate. Formation of phosphate esters generally does not require the addition of a mineral acid catalyst the way Fischer esterifications do. Explain why this is so.arrow_forwardComplete the given reactionarrow_forwardNAD is: B E) . Amines can be produced by: A) B) Oxidation of nitro compounds Reduction of nitro compounds Acidification of nitro compounds Hydrolysis of nitro compounds IUPAC name of the following compound is The reduced form of NADH A dehydrating coenzyme A hydrating coenzyme A methylating coenzyme The oxidized form of NADH A) 3-methylhexanoic acid 3-methylbenzoicacid 3-methylcyclohexanoic acid. 1-methylcyclohexanoic acid A) B) Peptide bonds are: A) B D) The compound 4-hydroxyhexanedioc acid has following functional groups (s) 2 Carboxylic acids alcohol and carboxylic acid ester and alcohol alcohol and aromatic group ක COOH Esters Amines Amides Carboxylic acids and amines CH₁ 3-metnyl кустоarrow_forward
- Both norepinephrine and epinephrine are synthesized from the same protein-derived amino acid. From which amino acid are they synthesized? What types of reactions are involved in their biosynthesis? н он H OH H HO. NH, НО. CH3 (a) (b) HO НО Norepinephrine Epinephrine (Adrenaline)arrow_forwardα-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. Draw the structures of the two intermediates formed in this reaction.arrow_forwardWhat product will result from the reaction shown? CHO amino alcohol amino acid imine CH3CH₂CH₂CH₂NH₂ enamine hydroxylamine H, Aarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
DIGESTER-35 | VITAMINS AND THEIR RELATED COENZYMES| GPAT | NIPER | PHARMACIST| DI; Author: GPAT DISCUSSION CENTER;https://www.youtube.com/watch?v=CGrdNYmho0s;License: Standard YouTube License, CC-BY