Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
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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H
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(i) Write the product obtained when D-glucose reacts with HCN.
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Chapter 19 Solutions
Essential Organic Chemistry, Global 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_forwardStep 7 of the citric acid cycle is shown. Which statement best describes what occurs in this step? CO₂ 1 CH || CH + H₂O CO₂ fumarate CO₂™ fumarase HO C-H CH₂ CO₂ malate A) Fumarate undergoes hydrogenation with hydrogens and electrons provided by the enzyme fumarase. B) Fumarate undergoes hydration with the aid of the enzyme fumarase. C) Fumarate undergoes hydrolysis with the aid of the enzyme fumarase. D) Fumarate undergoes reduction with the aid of the cofactor fumarase.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
- Draw the following compounds: Cellobiose: 2 glucose β-1,4arrow_forwardTPP 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.arrow_forwarda Lactate dehydrogenase H H3C-C-coO- ОН ooc-C-CH3 L-(+)-Lactase Pyruvate This is a(an) b Creatine kinase CH3 O CH3 O H2N, АТР ADP NH2 NH2 Adenosine triphosphate Adenosine diphosphate Creatine Phosphocreatine This is a(an)arrow_forward
- H-C -OH CH₂OPO₂²- 3-phosphoglycerate ATP ADP Arrow-pushing Instructions AC XT H-C-OH :O: CH₂OPO3²- =C² H-C-OH -O OPO3² Enz-SH 3 CH₂OPO3²- 1,3-bisphosphoglycerate ADP PO S-Enz H-C-OH CH₂OPO3²- One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. [Enzyme-bound thioester] NADH/H* NAD*, Enz-SH H H-C-OH CH₂OPO3²- Glyceraldehyde 3-phosphate :Ö: H-C-OH CH₂OPO3²- ADP 29arrow_forward4. Answer the following questions about the ketohexose 7 below. CH₂OH H-OH OH H CH₂OH 7 (i) Is the ketohexose 7 a natural D-sugar? Provide a short explanation for the answer. (ii) Draw the a-pyranose form of 7. +H HOarrow_forward(a) Are galactose and mannose constitutional isomers or stereoisomers? (b) Draw the structure of galactose 1-phosphate and mannose 6-phosphate. (c) Are these two phosphates constitutional isomers or stereoisomers?arrow_forward
- N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Nearrow_forwardНО Но н Н- НО он Н Н HO H OH оно н Н H. H Н ОН Н H н 아처 OH CH НО.arrow_forwardQ13: For the following reactions indicate whether the reaction involves a cofactor or coenzyme? A В COA HN CH2OPO3 *H,N NH2 CH2OPO CH,OH ATP AMP NH2 CoA P. Glutamine CoA H Mg2+ н но он OH H OH Phosphohexose 12 но isomerase 3 Phenylacetate (excess supplied) Phenylacetyl CoA OH H Phenylacetylglutamine (excreted) Glucose 6-phosphate Fructose 6-phosphate AGº= 1.7 kJ/molarrow_forward
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