Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 29.SE, Problem 31MP
Interpretation Introduction
Interpretation:
The amino acid cysteine, C3H7NO2S, is biosynthesized from a substance called cystathionine by a multistep pathway.
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If H218O is used in the hydrolysis reaction catalyzed by lysozyme, which ring will contain the label, NAMor NAG?
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.
Give the expected organic product when phenylacetic acid, PhCH2COOH, is treated with reagent
Q.)NaHCO3, H2O
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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- 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.arrow_forwardHyaluronic acid, a component of connective tissue, is the fluid that lubricates joints. It is a polymer of alternating N-acetyl-d-glucosamine and d-glucuronic acid subunits joined by β-1,3'-glycosidic linkages. Draw a short segment of hyaluronic acid.arrow_forwardThe following compound has been found to be an inhibitor of penicillinase. The enzyme can be reactivated by hydroxylamine (NH2OH). Propose a mechanism to account for the inhibition and for the reactivation.arrow_forward
- 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.arrow_forwardNaturally 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.arrow_forwardThe first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-R—CH2OH group by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.arrow_forward
- The 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_forwardOne of the steps in the biosynthesis of uridine monophosphate is the reaction of aspartate with carbamoyl phosphate to give carbamoyl aspartate followed by cyclization to form dihydroorotate. Propose mechanisms for both steps.arrow_forwardGive the expected organic product when phenylacetic acid, PhCH2COOH, is treated with reagent Q.)NaOH, H2Oarrow_forward
- If H218O is used in the hydrolysis reaction catalyzed by lysozyme, which ring will contain the label, NAM or NAG?arrow_forwardEthanolamine ammonia lyase, a coenzyme B12–requiring enzyme, catalyzes the following reaction. Propose a mechanism for this reaction.arrow_forwardTrehalose, C12H22O11, is a nonreducing sugar that is only 45% as sweet as sugar. When hydrolyzed by aqueous acid or the enzyme maltase, it forms only d-glucose. When it is treated with excess methyl iodide in the presence of Ag2O and then hydrolyzed with water under acidic conditions, only 2,3,4,6-tetra-O-methyl-d-glucose is formed. Draw the structure of trehalosearrow_forward
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