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, Problem 36P
there are two kinds of aldolases. Class I aldolases are found in animals and plants, whereas class II aldolases are found in fungi, algae, and some bacteria. Only class I aldolases form an imine. Class II aldolases have a metal ion (Zn2+) at the active site. The mechanism for catalysis by class I aldolases was described in Section 22.13. Propose a mechanism for catalysis by class II aldolases.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
There are two kinds of aldolases. Class I aldolases are found in animals and plants, whereas class II aldolases are found in fungi, algae, and some bacteria.Only class I aldolases form an imine. Class II aldolases have a metal ion (Zn2 + ) at the active site. The mechanism for catalysis by class I aldolases wasdescribed in Section 22.13. Propose a mechanism for catalysis by class II aldolases.
A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. If this reaction could be accomplished using H2 and a nickel catalyst, would the product be optically active? Explain.
A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. Is the product capable of showing optical activity? If it is, explain how.
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
- HW10 #21arrow_forwardThe formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forwardCan you help me understand how to approach this question and explain the mechanism?arrow_forward
- Show structures (in blank boxes) for the reactants/products in the following reactions.arrow_forwarda OH CH2CNHCH3 T CH3 d OH CHCHNHCH3 CH3 Ephedrine can be synthesized via reductive amination plus other necessary reactions. Predict the necessary reactants and reagents that will give the intermediate and final products shown.arrow_forwardDuring the acid catalyzed conversion of an aldehyde to a hemiacetal the acid reacts with the alsehyde to form a more elecrtophilic intermediate. What is the name of this intermediate?arrow_forward
- The product of this chloromethylation can be converted to piperonal, which is used in perfumery and in artificial cherry and vanilla flavors. How might the CH2Cl group of the chloromethylation product be converted to a CHO group?arrow_forwardhow the r-group affects the elimination, specifically E-1 reaction and how a different r-group would have a different effectarrow_forwardConsider the following reactions, and draw the products that are formed. Part 1 of 2 Draw the structure of the aldol condensation product that results from dimerization of the following aldehyde. You do not need to show stereochemistry. H* or HO H₂O Click and drag to start drawing a structure. × D: G P Part 2 of 2 Draw the structure of the aldol condensation product that results from dimerization of the following aldehyde. You do not need to show stereochemistry. H H+ or HO H₂O Click and drag to start drawing a structure. D: X 5 。arrow_forward
- One step in a recent short synthesis of a prostaglandin (Section 19.6) involves the conversion of succinaldehyde to the bicyclic hemiacetal X. Draw a stepwise mechanism for this process. (Hint: The mechanism begins with an intermolecular aldol reaction.)arrow_forwardIf a chemist attempted to carry out the coupling of the two a-ketoacids shown in the mechanism WITHOUT using the enzyme, what product (or products) would you expect? (I'm providing the whole mechanism here again to help you consider this question.) OH CH;- CH OH 00 CH CH;CH, R 10 B: H, ОН CH, CH, ČH,CH, R- HO `CH,CH3 CH CH,CH, CH CH;CH, HO HO `CH,CH3 НО `CH3 HO `CH3 CH,CH; A C D O only D all of these would be possible O only A O only B only Carrow_forwardIn Given reaction is a base-catalyzed epimerization reaction in which ketose is converted to a pair of aldoses. Predict the products?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher: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
Nucleic acids - DNA and RNA structure; Author: MEDSimplified;https://www.youtube.com/watch?v=0lZRAShqft0;License: Standard YouTube License, CC-BY