Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 25, Problem 25.29P
Interpretation Introduction
Interpretation:
The conversion of D-glucose-6-phosphate to D-fructose-6-phosphate as two enzyme catalysed keto-enol tautomerization has to be shown.
Concept Introduction:
The keto-enol tautomerization is said to be the interconversion of keto form to the enol form. The keto form is of carbonyl group and the enol form is of alcoholic group. The keto form products and enol form products are said to be Tautomers.
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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
Cholesterol-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 biosynthesis
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.
Chapter 25 Solutions
Organic Chemistry
Ch. 25.1 - Prob. 25.1PCh. 25.2 - Prob. 25.2PCh. 25.2 - Prob. 25.3PCh. 25.3 - Prob. 25.4PCh. 25.3 - Prob. 25.5PCh. 25.3 - Prob. AQCh. 25.3 - Prob. BQCh. 25.3 - Prob. CQCh. 25.3 - Prob. DQCh. 25.3 - How many stereoisomers would result from the...
Ch. 25.4 - Prob. 25.6PCh. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10PCh. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Prob. 25.31PCh. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Prob. 25.34PCh. 25 - In making candy or sugar syrups, sucrose is boiled...Ch. 25 - Prob. 25.36PCh. 25 - Prob. 25.37PCh. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - Prob. 25.41PCh. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Digitalis is a preparation made from the dried...Ch. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50P
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