Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 29.SE, Problem 51AP
In glycerol
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Draw the Fischer projection of the product of the reaction of D-
glyceraldehyde-3-phosphate catalyzed by glyceraldehyde-3-phosphate-
dehydrogenase in this step in glycolysis. Provide the structure in the
protonation state found in physiological conditions.
H
OH
OPO2-
H
Drawing
。
glyceraldehyde-3-
phosophate
dehydrogenase
NAD+, Pi
NADH
Imidazoleglycerol‑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.
Step 7 of the citric acid cycle is shown. Which statement best describes what occurs
in this step?
CO₂
1
CH
||
CH
+ H₂O
CO₂
fumarate
CO₂™
fumarase HO C-H
CH₂
CO₂
malate
A)
Fumarate undergoes hydrogenation with hydrogens and electrons provided
by the enzyme fumarase.
B) Fumarate undergoes hydration with the aid of the enzyme fumarase.
C) Fumarate undergoes hydrolysis with the aid of the enzyme fumarase.
D) Fumarate undergoes reduction with the aid of the cofactor fumarase.
Chapter 29 Solutions
Organic Chemistry
Ch. 29.1 - Prob. 1PCh. 29.3 - Write the equations for the remaining passages of...Ch. 29.3 - Prob. 3PCh. 29.4 - Write a mechanism for the dehydration reaction of...Ch. 29.4 - Evidence for the role of acetate in fatty-acid...Ch. 29.4 - Does the reduction of acetoacetyl ACP in step 6...Ch. 29.5 - Prob. 7PCh. 29.5 - Look at the entire glycolysis pathway, and make a...Ch. 29.6 - Prob. 9PCh. 29.7 - Prob. 10P
Ch. 29.7 - Write mechanisms for step 2 of the citric acid...Ch. 29.7 - Prob. 12PCh. 29.8 - Prob. 13PCh. 29.9 - Write all the steps in the transamination reaction...Ch. 29.9 - What -keto acid is formed on transamination of...Ch. 29.9 - Prob. 16PCh. 29.SE - Prob. 17VCCh. 29.SE - Identify the following intermediate in the citric...Ch. 29.SE - The following compound is an intermediate in the...Ch. 29.SE - Prob. 20VCCh. 29.SE - In the pentose phosphate pathway for degrading...Ch. 29.SE - Prob. 22MPCh. 29.SE - One of the steps in the pentose phosphate pathway...Ch. 29.SE - One of the steps in the pentose phosphate pathway...Ch. 29.SE - Prob. 25MPCh. 29.SE - Prob. 26MPCh. 29.SE - Prob. 27MPCh. 29.SE - Prob. 28MPCh. 29.SE - Prob. 29MPCh. 29.SE - Prob. 30MPCh. 29.SE - Prob. 31MPCh. 29.SE - Prob. 32APCh. 29.SE - Prob. 33APCh. 29.SE - Prob. 34APCh. 29.SE - Prob. 35APCh. 29.SE - Prob. 36APCh. 29.SE - Prob. 37APCh. 29.SE - Prob. 38APCh. 29.SE - Prob. 39APCh. 29.SE - Prob. 40APCh. 29.SE - Prob. 41APCh. 29.SE - Prob. 42APCh. 29.SE - Prob. 43APCh. 29.SE - Prob. 44APCh. 29.SE - Prob. 45APCh. 29.SE - Prob. 46APCh. 29.SE - Prob. 47APCh. 29.SE - Prob. 48APCh. 29.SE - Prob. 49APCh. 29.SE - Prob. 50APCh. 29.SE - In glycerol metabolism, the oxidation of...Ch. 29.SE - Prob. 52APCh. 29.SE - Prob. 53APCh. 29.SE - Prob. 54APCh. 29.SE - In step 7 of fatty-acid biosynthesis (Figure...Ch. 29.SE - Prob. 56AP
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- The same E1–E2–E3 multienzyme structure found in the pyruvate dehydrogenase and the a-ketoglutarate dehydrogenase complexes is also used in the branched-chain a-ketoacid dehydrogenase complex, which participates in the catabolism of branched-chain amino acids. Draw the reaction product when the following substrate is acted on by the branched-chain a-keto acid dehydrogenase complex.arrow_forwardH-C-U-o 27. The following is step 3 of the citric acid cycle. What is the functional transformation that occurs in the first part of this step? group COO COO NAD* NADH + H* CH2 CH2 0 H-C-C CH2 H-C-H H-C-COO- Но-с-н COO COO Isocitrate a-ketoglutarate A) A ketone and an alcohol change positions. C) The -COO is transformed. B) An alcohol becomes a ketone. D) The alcohol becomes an aldehyde. 28. The following is step 3 of the citric acid cycle. What is the identity of the Molecule represented by I? COO COO NAD* NADH + H* I COO CH2 CH2 0 H-C-C CH2 H-C-H H-C-COO- HO-C-H COO COO Isocitrate a-ketoglutarate A) Acetate B) GTP C) NADH D) FADH2 E) CO2arrow_forwardTPP is a coenzyme for transketolase, the enzyme that catalyzes the conversion of a ketopentose (xylulose5-phosphate) and an aldopentose (ribose-5-phosphate) to an aldotriose (glyceraldehyde-3-phosphate) and a ketoheptose (sedoheptulose-7-phosphate). Notice that the total number of carbons in the reactants and products is the same (5 + 5 = 3 + 7). Propose a mechanism for this reaction.arrow_forward
- Selective and specific inhibitors of acetyl-CoA carboxylase have been proposed to be potential anti-obesity drugs. (i) What is the effect of an inhibitor of acetyl-CoA carboxylase on fatty acid synthesis and fatty acid oxidation? Figure 5 shows the structures of the inhibitors of acetyl-CoA carboxylase: CABI-COA and CABI. What structural features of CABI make it a potential inhibitor of acetyl-CoA carboxylase?arrow_forwardIf an enzyme-catalyzed reaction has a high rate at low pH and low rate at higher pH, this implies that a group on either the enzyme or the substrate must be for an efficient reaction. leaving group oxidoreductase coenzymes O protonated deprotonated The compound that consists of deoxyribose linked by an N-glycosidic bond to N-9 of guanine is: adenylate deoxyguanosine guanosine nucleotide guanylatearrow_forwardDraw the product of the following metabolic reaction. HCO3, ATP CH3CSC0A ADP + P₁ + H+ N-Carboxybiotin • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Consider E/Z stereochemistry of alkenes. • In cases where there is more than one answer, just draw one. • Use R1 to represent coenzyme A and acyl carrier protein. The R group tool is located in the charges and lone pairs drop-down menu.arrow_forward
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