Introduction to General, Organic and Biochemistry
12th Edition
ISBN: 9780357119303
Author: Bettelheim, Frederick A., Brown, William H., Campbell, Mary K., FARRELL, Shawn O., Torres, Omar
Publisher: Cengage Learning
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Chapter 19, Problem 68P
Interpretation Introduction
Interpretation: The enzyme-catalyzed conversion of dihydroxyacetone phosphate to D-glyceraldehyde-3-phosphate should be shown as two-enzyme keto-enol tautomerizations.
Concept Introduction: The
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One pathway for the metabolism of D-glucose 6-phosphate is its enzyme-catalyzed
conversion to D-fructose 6-phosphate. Show that this transformation can be accom-
plished as two enzyme-catalyzed keto-enol tautomerisms.
СНО
CH,OH
C=0
enzyme
catalysis
Но
Но
H
OH
H
H.
O-
H-
-HO-
ČH,OPO,
ČH,OPO,
D-Glucose 6-phosphate
D-Fructose 6-phosphate
4. Glycolysis is a metabolic pathway that converts glucose into pyruvate while synthesizing
high-energy molecules. During one step of Glycolysis, glucose-6-phosphate (an aldose) is
converted to fructose-6-phosphate (a ketose) via an ene-diol intermediate.
OH OH O
OP OH OH
ОН
ОН
glucose-6-phosphate
OH OH OH
OP OH
fructose-6-phosphate
Draw arrow pushing mechanism to describe this isomerization. Use B: and HA as surrogates
for basic/acidic amino acid residues.
Vanillin (4-hydroxy-3-methoxybenzaldehyde), the principal component of vanilla, occurs in vanilla beans and other natural sources as a b-d-glucopyranoside. Draw a structural formula for this glycoside, showing the d-glucose unit as a chair conformation.
Chapter 19 Solutions
Introduction to General, Organic and Biochemistry
Ch. 19.1 - Prob. 19.1QCCh. 19.1 - Prob. 19.2QCCh. 19.2 - Prob. 19.3QCCh. 19.3 - Prob. 19.4QCCh. 19.4 - Prob. 19.5QCCh. 19.5 - Prob. 19.6QCCh. 19 - Prob. 1PCh. 19 - Prob. 2PCh. 19 - Prob. 3PCh. 19 - Prob. 4P
Ch. 19 - Prob. 5PCh. 19 - Prob. 6PCh. 19 - Prob. 7PCh. 19 - Prob. 8PCh. 19 - Prob. 9PCh. 19 - Prob. 10PCh. 19 - Prob. 11PCh. 19 - Prob. 12PCh. 19 - Prob. 13PCh. 19 - Prob. 14PCh. 19 - Prob. 15PCh. 19 - Prob. 16PCh. 19 - Prob. 17PCh. 19 - Prob. 18PCh. 19 - Prob. 19PCh. 19 - Prob. 20PCh. 19 - Prob. 21PCh. 19 - Prob. 22PCh. 19 - Prob. 23PCh. 19 - Prob. 24PCh. 19 - Prob. 25PCh. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - Prob. 28PCh. 19 - Prob. 29PCh. 19 - Prob. 30PCh. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - Prob. 33PCh. 19 - Prob. 34PCh. 19 - Prob. 35PCh. 19 - Prob. 36PCh. 19 - Prob. 37PCh. 19 - Prob. 38PCh. 19 - Prob. 39PCh. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - 6 Where is glycogen stored in the human body?Ch. 19 - Prob. 43PCh. 19 - 8 How is it possible that cows can digest grass...Ch. 19 - 1 Hyaluronic acid acts as a lubricant in the...Ch. 19 - Prob. 46PCh. 19 - Prob. 47PCh. 19 - Prob. 48PCh. 19 - Prob. 49PCh. 19 - Prob. 50PCh. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - Prob. 54PCh. 19 - Prob. 55PCh. 19 - Prob. 56PCh. 19 - Prob. 57PCh. 19 - Prob. 58PCh. 19 - Prob. 59PCh. 19 - Prob. 60PCh. 19 - Prob. 61PCh. 19 - Prob. 62PCh. 19 - Prob. 63PCh. 19 - Prob. 64PCh. 19 - Prob. 65PCh. 19 - Prob. 66PCh. 19 - Prob. 67PCh. 19 - Prob. 68PCh. 19 - Prob. 69PCh. 19 - Prob. 70PCh. 19 - Prob. 71PCh. 19 - Prob. 72PCh. 19 - Prob. 73PCh. 19 - Prob. 74PCh. 19 - Prob. 75P
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- Cellobiose, a disaccharide obtained by the hydrolysis of cellulose, is composed of two glucose units joined together in a 1→4-β-glycoside bond. What is the structure of cellobiose?arrow_forwardThe following is the structure of salicin, a bitter-tasting compound found in the bark of willow trees: The aromatic ring portion of this structure is quite insoluble in water. How would forming a glycosidic bond between the aromatic ring and β - D -glucose alter the solubility?arrow_forwardCholesterol-lowering drugs commonly target O HMG-COA synthase, the enzyme that catalyzes the synthesis of mevalonate O pyruvate decarboxylase complex, which catalyzes the synthesis of acetyl-CoA O mevalonate, an isoprene O HMG-COAreductase, the rate-limiting enzyme in cholesterol biosynthesis O HMG-CoA synthase, the enzyme that catalyzes the first step in cholesterol biosynthesisarrow_forward
- 4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОНarrow_forwardA graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. Is the product capable of showing optical activity? If it is, explain how.arrow_forwardH CH3 H₂C-N-CH₂-C-CH₂- CH3 OH The reason that this compound is required in the diet of humans is that it: O is part of the coenzyme A molecule. O helps fatty acids cross the inner mitochondrial membrane. O is involved in the reoxidation of cytosolic NADH under anaerobic conditions. O is a precursor of one of the most important oxidizing agents in cells. O is part of the flavin adenine dinucleotide molecule. EESarrow_forward
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