Can you help me understand how to approach this question and explain the mechanism? Glucuronic acid is an oxidized derivative of glucose found in animal secretions such as saliva. Biologicalconversion of glucuronic acid into its isomer, fructuronic acid, is catalyzed by an enzyme called uronic acidisomerase.OHHOHOH20, H*НОНо-Но-НОHOuronic acid isomeraseНоОНfructuronic acidglucuronic acidProvide a complete curved-arrow mechanism for this transformation. You may assume that the enzymeactive site will supply all necessary equivalents of water and acid in order to accomplish the reaction. (In otherwords, draw the mechanism as if the only reagents were H3O* and H20.)

First step of this reaction is protonation where glucuronic acid is attacked by H+ ion in the…

Glucuronic acid is an oxidized derivative of glucose found in animal secretions such as saliva. Biological conversion of glucuronic acid into its isomer, fructuronic acid, is catalyzed by an enzyme called uronic acid isomerase. OH HO HOʻ H20, H* HỌ HO Но ОН ОН uronic acid isomerase HO ОН fructuronic acid glucuronic acid Provide a complete curved-arrow mechanism for this transformation. You may assume that the enzyme active site will supply all necessary equivalents of water and acid in order to accomplish the reaction. (In other words, draw the mechanism as if the only reagents were H3O* and H20.)

Glucuronic acid is an oxidized derivative of glucose found in animal secretions such as saliva. Biological conversion of glucuronic acid into its isomer, fructuronic acid, is catalyzed by an enzyme called uronic acid isomerase. OH HO HOʻ H20, H* HỌ HO Но ОН ОН uronic acid isomerase HO ОН fructuronic acid glucuronic acid Provide a complete curved-arrow mechanism for this transformation. You may assume that the enzyme active site will supply all necessary equivalents of water and acid in order to accomplish the reaction. (In other words, draw the mechanism as if the only reagents were H3O* and H20.)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter17: Alcohols And Phenols

Section17.SE: Something Extra

Problem 73AP

See similar textbooks

Similar questions

One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to glucose 6-phosphate. Propose a mechanism, using acid or base catalysis as needed.
d-Glucuronic acid is found widely in plants and animals. One of its functions is to detoxify poisonous HO-containing compoundsby reacting with them in the liver to form glucuronides. Glucuronides are water soluble and therefore readily excreted. Afteringestion of a poison such as turpentine or phenol, the glucuronides of these compounds are found in the urine. Draw thestructure of the a- and b-glucuronides formed by the reaction of b-d-glucuronic acid and phenol.
What is the product 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
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.
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.
d-Glucuronic acid is found widely in plants and animals. One of its functions is to detoxify poisonous HO-containing compounds by reacting with them in the liver to form glucuronides. Glucuronides are water soluble and, therefore, readily excreted. After ingestion of a poison such as turpentine or phenol, the glucuronides of these compounds are found in urine. Draw the structure of the glucuronide formed by the reaction of beta-d-glucuronic acid and phenol.
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
Several 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.
Fats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products.
Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.
The rate constant for the uncatalyzed reaction of two molecules of glycine ethyl ester to form glycylglycine ethyl ester is 0.6 M- 1s - 1. In the presence of Co2 +, the rate constant is 1.5 * 106 M- 1s - 1. What rate enhancement does the catalyst provide?