НООССH-CHCOOН + Н,О. H,SO, - HOOCCH,CH(OH)COOH This reaction is also an important reaction of the tricarboxylic acid cycle in cells, wherein the reaction occurs in neutral solution, so the acid groups are both ionized to the carboxylate form. The reaction is catalyzed by the stereospecific enzyme fumarase that utilizes only the trans form of 2-butenedioate ion, also known as fumarate, and produces only the (S)-2-hydroxysuccinate enantiomer,also known as (S)-malate. fumarase fumarate + H,O • • (S)-malate Draw the correct stereochemical structures of these two compounds of the fumarase-catalyzed reaction. Be sure to include all hydrogen atoms and show the carboxylates as anions. Clearly draw a wedged bond, a dashed bond and two in-plane bonds for the chiral carbon.

НООССH-CHCOOН + Н,О. H,SO, - HOOCCH,CH(OH)COOH This reaction is also an important reaction of the tricarboxylic acid cycle in cells, wherein the reaction occurs in neutral solution, so the acid groups are both ionized to the carboxylate form. The reaction is catalyzed by the stereospecific enzyme fumarase that utilizes only the trans form of 2-butenedioate ion, also known as fumarate, and produces only the (S)-2-hydroxysuccinate enantiomer,also known as (S)-malate. fumarase fumarate + H,O • • (S)-malate Draw the correct stereochemical structures of these two compounds of the fumarase-catalyzed reaction. Be sure to include all hydrogen atoms and show the carboxylates as anions. Clearly draw a wedged bond, a dashed bond and two in-plane bonds for the chiral carbon.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.69P

See similar textbooks

Similar questions

please explain why this happends, im having trouble in this section. Part A Chymotrypsin, an enzyme that hydrolyzes peptide bonds in proteins, functions in the small intestine at an optimum pH of 7.7 to 8.0. How is the rate of the chymotrypsin-catalyzed reaction affected by each of the following conditions?
When some sugars dissolve in water they spontaneously undergo changes in optical rotation called mutarrotation. The Mutarrotation of D-glucopyranose is catalyzed by acid and bases. 2-Hydroxypyridine is a more effective catalyst than phenol and pyridine for this reaction because: a.Both oxygen and N in 2-hydroxypyridine act as bases increasing the rapid interconversion of sugar b. The OH of 2-hydroxypyridine serves as the base while the current N as the acid. c. 2-hydroxypyridine acts both as a base to remove the proton from the hydroxyl group in the hemiacetal and as an acid to provide a proton to the oxygen in the hemiacetal. d.Phenol and pyridine are very expensive.
In Problem 7.28, we saw this two-step sequence in Johnsons synthesis of the steroid hormone progesterone. Propose a structural formula for the intermediate formed in Step 3 and a mechanism for its conversion in Step 4 to progesterone.
Polyunsaturated fatty acids (PUFA's) in oils 0.g. sunflower oil are prone to rancidity because they contain conjugated double bond systems which are easily oxidized in the presence of light or peroxides. BHT Is used as an antioxidant in oils to prevent oxidative rancidity. How do BHT prevent oils from reacting with peroxides so that they do not become rancid? Show the mechanism.
Choose two correct answers. The first reaction below ( the one on the left) is catalyzed by carbonic anhydrase. The carbonic acid product can to bicarbonate and a protein. CO2 +H2O__ H2CO3__HCO3- +H+ A- Removal of CO2 shifts the reaction toward reactants. B- Removal of CO2 shifts the equilibrium towards products. C- Ionization to bicarbonate disfavors the forward reaction of CA. D- Removal of protons pulls the reaction toward products. E- Position of equilibrium does not depend on concentration of reactants.
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.
What is the product (from the image below) of the starting material D-glyceraldehyde which will (1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3 (2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3
Define the following terms: a. reaction mechanism b. carbocation c. enediol d. general acid e. general base
What is the mechanism for this reaction? We get the hint that after the Grignard-reaction there is a intramolekular reaction with the ester (CO2Et-group).
Identify X and Y, two mtamediates m the synthesis of the antidepressant venlafaxme (effexor) m the following reaction scheme.
Illustrate mechanisam for the hydrolysis of an acide chloride ?
Ozonolysis, osmylation, and epoxide formation with mCPBA are all what type of reactions? a.) reduction b.)oxidation c) bothd) neither