Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 19, Problem 44P
Interpretation Introduction
Interpretation:
Fructose-1,6-bisphosphate labeled at C-3 and C-4 is obtained when
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TPP is a coenzyme for transketolase, the enzyme that catalyzes the conversion of a ketopentose (xylulose- 5-phosphate) and an aldopentose (ribose-5-phosphate) to an aldotriose (glyceraldehyde-3-phosphate) anda ketoheptose (sedoheptulose-7-phosphate). Notice that the total number of carbons in the reactants and products is the same (5 + 5 = 3 + 7). Propose a mechanism for this reaction.
Draw a Haworth projection for the disaccharide gentibiose, given the following information:(a) It is a dimer of glucose.(b) The glycosidic linkage is B(1 -> 6).(c) The anomeric carbon not involved in the glycosidic linkage isin the B configuration.
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Q.) What is the specific rotation of a-l-glucose?
Chapter 19 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 19.4 - Prob. 1PCh. 19.4 - How many molecules of NADH are formed from the...Ch. 19.4 - Why does the OH group add to the -carbon rather...Ch. 19.5 - Prob. 4PCh. 19.5 - Prob. 5PCh. 19.5 - The oxidation of glyceraldehyde-3-phosphate to...Ch. 19.5 - Prob. 7PCh. 19.6 - Prob. 8PCh. 19.6 - Prob. 9PCh. 19.6 - Propose a mechanism for the reduction of...
Ch. 19.7 - Prob. 11PCh. 19.8 - Acid-catalyzed dehydration reactions are normally...Ch. 19.8 - Prob. 13PCh. 19.8 - Prob. 14PCh. 19.8 - Prob. 15PCh. 19.9 - Prob. 16PCh. 19.10 - a. What is the name of the enzyme that converts...Ch. 19.13 - 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 - Prob. 42PCh. 19 - Prob. 43PCh. 19 - Prob. 44PCh. 19 - UDP-galactose-4-epimerase converts UDP-galactose...Ch. 19 - A student is trying to determine the mechanism for...Ch. 19 - What would be the results of the experiment in...
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- One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose 5-phosphate with ribose 5-phosphate in the presence of a transketolase to give glyceraldehyde 3-phosphate and sedoheptulose 7-phosphate. (a) The first part of the reaction is nucleophilic addition of thiamin diphosphate (TPP) ylide to xylulose 5-phosphate, followed by a retro-aldol cleavage to give glyceraldehyde 3-phosphate and a TPPcontaining enamine. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is addition of the enamine to ribose 5-phosphate followed by loss of TPP ylide to give sedoheptulose 7-phosphate. Show the mechanism.arrow_forwardDraw the following compounds: Cellobiose: 2 glucose β-1,4arrow_forwardWhat would be the haworth projection of a beta D-aldohexose carbohydrate?arrow_forward
- Which of the following glycosidic linkage is found in maltose? * A. Glucose (a1-2B) Fructose B. Glucose (a1-4) Glucose C. Galactose (B1-4) Glucose D. Glucose (B1-4)Glucosearrow_forwardIdentify the sugar in each description. a. An aldopentose that is not d-arabinose forms d-arabinitol when it is reduced with NaBH4. b. A sugar that is not D-altrose forms d-altraric acid when it is oxidized with nitric acid. c. A ketose that, when reduced with NaBH4, forms d-altritol and d-allitol.arrow_forwarddraw a haworth structure of fructose as a 5 membered ring in the b form, and as a 6-membered ring in the a formarrow_forward
- The standard free energy change (ΔG°') for hydrolysis of fructose-l,6-bisphosphate (FBP) to fructose-6-phosphate (F-6-P) and Pi is -16.7 kJ/mol: FBP + H2O → Fructose-6-P + Pi The standard free energy change (ΔG°') for ATP hydrolysis is -30.5 kJ/mol: ATP + H2O → ADP + Pi a What is the standard free energy change for the phosphofructokinase reaction: ATP + Fructose-6-phosphate → ADP + FBP ΔG°' = -13.8 kJ/mol b What is the equilibrium constant for this reaction at 25.0 °C? K'eq =arrow_forwardDoes the [1,7] sigmatropic rearrangement that converts provitamin D3 to vitamin D3 involve suprafacial or antarafacial rearrangement?arrow_forwardDraw the following compounds and please provide a clear picture C-3 epimer of Fructosearrow_forward
- Stachyose is an oligosaccharide found in high concentrations of beans. Stachyose is composed of alpha-D-galactopyranosyl-(1-6)-alpha-D-galactopyranosyl-(1-6)-alpha-D-glucopyranosyl-(1-2)beta-D- fructofuranose . Draw the structure of stachyose using Haworth projections.arrow_forwardDeduce the structure of the disaccharide isomaltose from the following data.a. Hydrolysis yields D-glucose exclusively. b. Isomaltose is cleaved with α-glycosidase enzymes. c. Isomaltose is a reducing sugar. d. Methylation with excess CH3I, Ag2O and then hydrolysis with H3O+ forms two products:arrow_forwardIdentify the sugar in description. An aldopentose that is not d-arabinose forms d-arabinitol when it is reduced with NaBH4.arrow_forward
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