![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9780321803221/9780321803221_largeCoverImage.gif)
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 24, Problem 28P
What acyl groups have we seen transferred by reactions thiamine pyrophosphate as a coenzymes? (Hint: See problems 9, 10, 11, 27, and 28.)
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Want to see the full answer?
Check out a sample textbook solution![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
One of these reactions is a reductive amination.
Write the oxidation states ( a number) next to each boxed carbon.
Which reaction is a reductive amination? A or B
Identify the oxidized and reduced states of the coenzymes
Triosephosphate isomerase (TIM) catalyzes the conversion of dihydroxyacetone phosphate to glyceraldehyde-3-phosphate. The enzyme’s catalytic groups are Glu 165 and His 95. In the first step of the reaction, these catalytic groups function as a general-base and a general-acid catalyst, respectively. Propose a mechanism for the reaction.
None
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.2 - How many conjugated double bonds are there in a....Ch. 24.2 - Instead of adding to the 4a position and...Ch. 24.2 - Prob. 7PCh. 24.3 - Prob. 8PCh. 24.3 - Acetolactate synthase is another TPP-requiring...Ch. 24.3 - Acetolactate synthase transfers the acyl group of...Ch. 24.5 - Prob. 12PCh. 24.5 - The enzyme that catalyzes the C C bond cleavage...
Ch. 24.5 - Propose a mechanism for the ,-elimination reaction...Ch. 24.5 - Which compound is more easily decarboxylated?Ch. 24.5 - Explain why the ability of PLP to catalyze an...Ch. 24.5 - Explain why the ability of PLP to catalyze an...Ch. 24.6 - Ethanolamine ammonia lyase, a coenzyme...Ch. 24.6 - Prob. 19PCh. 24.7 - How do the structure of tetrahydrofolate and...Ch. 24.7 - What is the source of the methyl group in...Ch. 24.8 - Thiols such as ethanethiol and propanethiol can be...Ch. 24 - How does the metal ion in carboxypeptidase A...Ch. 24 - Prob. 23PCh. 24 - Prob. 24PCh. 24 - Prob. 25PCh. 24 - S-Adenosylmethionine (SAM) is formed from the...Ch. 24 - Prob. 27PCh. 24 - What acyl groups have we seen transferred by...Ch. 24 - Propose a mechanism for the following reaction:Ch. 24 - When transaminated, the three branched-chain amino...Ch. 24 - Draw the products of the following reaction, where...Ch. 24 - When UMP is dissolved in T2O, exchange of T for H...Ch. 24 - Dehydratase is a PLP-requiring enzyme that...Ch. 24 - In addition to the reaction mentioned in Section...Ch. 24 - PLP can catalyze both ,-elimination reactions...Ch. 24 - The glycine cleavage system is a group of four...Ch. 24 - Prob. 37PCh. 24 - FADH2 reduces , -unsaturated thioesters to...
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
- One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose 5-phosphate with ribose 5-phosphate in the presence of a transketolase to give glyceraldehyde 3-phosphate and sedoheptulose 7-phosphate. (a) The first part of the reaction is nucleophilic addition of thiamin diphosphate (TPP) ylide to xylulose 5-phosphate, followed by a retro-aldol cleavage to give glyceraldehyde 3-phosphate and a TPPcontaining enamine. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is addition of the enamine to ribose 5-phosphate followed by loss of TPP ylide to give sedoheptulose 7-phosphate. Show the mechanism.arrow_forwardThe vitamin Niacin is used to form nicotinamide adenosine dinucleotide, which readily shuttles between its oxidized (NAD+) and reduced (NADH) forms. The latter serves as a cellular equivalent to NaBH4. The essential portions of the structures are shown below. Outline a mechanism for the cellular conversion of pyruvate to lactate. (Note: like NaBH4, NADH cannot reduce carboxylic acid carbonyls).arrow_forwardIn the body, during the citric acid cycle the following reaction occurs as the first part of an enzyme mediated process. но OH YYYYYY OH OH H₂O NaBH4 LiAlH4 H₂SO4 and heat K₂Cr2O7 HQ OH What reagent would be used to bring about this reaction in the laboratory? OH 3arrow_forward
- ter 18 em 18.18 Part A What coenzyme picks up hydrogen when a carbon-oxygen double bond is formed? Express your answers as a chemical expression. ΑΣΦ Submit Previous Answers Request Answer X Incorrect; Try Again; 3 attempts remalning ide Feedback (१ ।arrow_forwardWhich coenzyme is responsible for the following reaction? CO,H CO,H OH HO.. ОН ОН ОН O TPP (thiamine pyrophosphate) O NAD* (or NADP*) Ο ΚΗ2 O FADH2 В12 O PLP (pyridoxal phosphate) O one of the THE (tetrahydrofolate) coenzymes O NADH (or NADPH) O biotin O FADarrow_forwardImidazoleglycerol‑phosphate dehydratase is an enzyme in the histine biosynthesis pathway. It catalyzes the E1 dehydration of D‑erthyro‑imidazole‑glycerol phosphate to imidazole acetol‑phosphate. This is a rare example of a biological E1 reaction, as most biological elimination reactions occur through E1cB instead. In this reaction, D‑erthyro‑imidazole‑glycerol phosphate is first protonated to form a good leaving group. Then, the leaving group is ejected to form the resonance‑stabilized carbocation shown. Draw curved arrows forming the most stable resonance structure to explain why this reaction goes through an E1 mechanism. Draw curved arrows to form the most stable resonance structure.arrow_forward
- How would you describe the glycosidic bond in the following molecule? OH OH HOH H 0- H. но H ОН Он Н H OH OH H. alpha-1,4- beta-1,4- alpha-1,6- beta-1,6- none of thesearrow_forwardExplain why the half-life (the time it takes for one-half of the compound to be metabolized) of Xylocaine is longer than that of Novocaine.arrow_forwardThe given mechanism of transamination reaction is shown below, To complete the shuffling of amino groups and carbonyls, the PMP must be converted back to PLP. How would you predict that this occurs? 1. A separate reaction oxidizes the amine group of PMP to an aldehyde. 2. A separate reaction hydrolyzes the amine of PMP to an aldehyde. 3. A different ketoacid reacts with the amine of PMP, and the entire sequence runs backward. 4. Either 2 or 3 could occur.arrow_forward
- One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of sedoheptulose 7-phosphate with glyceraldehydes 3-phosphate in the presence of a transaldolase to yield erythrose 4-phosphate and fructose 6-phosphate. (a) The first part of the reaction is the formation of a protonated Schiff base of sedoheptulose 7-phosphate with a lysine residue in the enzyme followed by a retro-aldol cleavage to give an enamine plus erythrose 4-phosphate. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is a nucleophilic addition of the enamine to glyceraldehyde 3-phosphate followed by hydrolysis of the Schiff base to give fructose 6-phosphate. Show the mechanism.arrow_forward26. Cyclophosphamide is a prodrug converted to nitrogen mustard as shown in the following scheme. Cyclophosphamide is thus classified as HÖ) CI P450 H2N P-N Cyclophosphamide B: H2N H. HPO, + NH3 + HN spontaneous OR phosphoramidase A. Bipartate prodrug B. Tripartite prodrug C. Bioprecursor prodrug D. Mutual prodrugarrow_forwardGlyceryl tricaprate (or tricaprin) is a triacylglycerol used in foods, drugs, and cosmetics as an additive. What will be the products of the complete acid/enzymatic hydrolysis of glyceryl tricaprate, as shown below? 0 CH₂-0 HT, heat or lipase + 3H₂O CH-0 CH₂2-0 Glyceryl tricaprate O one glycerol molecule and one capric acid molecule O one glycerol molecule and three capric acid molecules O two glycerol molecules and four capric acid molecules O two glycerol molecules and two capric acid molecules 0 0arrow_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 Learning
- Introductory Chemistry: A FoundationChemistryISBN:9781337399425Author:Steven S. Zumdahl, Donald J. DeCostePublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781285869759/9781285869759_smallCoverImage.gif)
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
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781133951889/9781133951889_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781337399425/9781337399425_smallCoverImage.gif)
Introductory Chemistry: A Foundation
Chemistry
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
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