EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 29.SE, Problem 23MP
One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of sedoheptulose 7-phosphate with glyceraldehydes 3-phosphate in the presence of a transaldolase to yield erythrose 4-phosphate and fructose 6-phosphate.
(a) The first part of the reaction is the formation of a protonated Schiff base of sedoheptulose 7-phosphate with a lysine residue in the enzyme followed by a retro-aldol cleavage to give an enamine plus erythrose 4-phosphate. Show the structure of the enamine and the mechanism by which it is formed.
(b) The second part of the reaction is a nucleophilic addition of the enamine to glyceraldehyde 3-phosphate followed by hydrolysis of the Schiff base to give fructose 6-phosphate. Show the mechanism.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Please label this HNMR
Consider the following gas chromatographs of Compound A, Compound B, and a mixture of Compounds A and B.
Inject
A
B
mixture
Area= 9
Area = 5
Area = 3
Area
Inject
.
མི།
Inject
J2
What is the percentage of Compound B in the the mixture?
Rank these according to stability.
CH3
H3C
CH3
1
CH3
H3C
1 most stable, 3 least stable
O 1 most stable, 2 least stable
2 most stable, 1 least stable
O2 most stable, 3 least stable
O3 most stable, 2 least stable
O3 most stable, 1 least stable
CH3
2
CH3
CH3
H₂C
CH3
3
CH3
CH
Chapter 29 Solutions
EBK 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
Additional Science Textbook Solutions
Find more solutions based on key concepts
Sea turtles have disappeared from many regions, and one way of trying to save them is to reintroduce them to ar...
MARINE BIOLOGY
An obese 55-year-old woman consults her physician about minor chest pains during exercise. Explain the physicia...
Biology: Life on Earth with Physiology (11th Edition)
What were the major microbiological interests of Martinus Beijerinck and Sergei Winogradsky? It can be said tha...
Brock Biology of Microorganisms (15th Edition)
Label each statement about the polynucleotide ATGGCG as true or false. The polynucleotide has six nucleotides. ...
General, Organic, and Biological Chemistry - 4th edition
Identify each of the following reproductive barriers as prezygotic or postzygotic. a. One lilac species lives o...
Campbell Essential Biology with Physiology (5th Edition)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Consider this IR and NMR: INFRARED SPECTRUM TRANSMITTANCE 0.8- 0.6 0.4 0.2 3000 10 9 8 00 HSP-00-541 7 CO 6 2000 Wavenumber (cm-1) сл 5 ppm 4 M Which compound gave rise to these spectra? N 1000 1 0arrow_forwardConsider this reaction (molecular weights are under each compound): HC=CH + 2 HCI --> C2H4Cl 2 MW = 26 36.5 99 If 4.4 g of HC=CH are reacted with 110 mL of a 2.3 M HCI solution, and 6.0 g of product are actually produced, what is the percent yield?arrow_forwardWhat is the name of the major product of this reaction? OH CH3 H₂SO4, heat 1-methylcyclohexene O2-methyl-1-cyclohexene O 3-mthylcyclohexene 1-methyl-2-cyclohexenearrow_forward
- We added a brown solution of Br2 to one of our products, and the brown color disappeared. This indicated that our product wasarrow_forwardRank the following according to reactivity toward nitration: a) benzene b) bromobenzene c) nitrobenzene d) phenol Od) greatest, c) least Od) greatest, b) least Od) greatest, a) least a) greatest, b) least a) greatest, c) least Oa) greatest, d) least Ob) greatest, a) least O b) greatest, c) least Ob) greatest, d) least O c) greatest, a) least O c) greatest, b) least O c) greatest, d) leastarrow_forwardO-Nitrophenol was distilled over with the steam in our experiment while the other isomer did not. This is due to: O intramolecular hydrogen bonding in the ortho isomer O intermolecular hydrogen bonding in the the ortho isomer O the ortho isomer has a lower density O the ortho isomer has a lower molecular weightarrow_forward
- K 44% Problem 68 of 15 Submit Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. :6: :: :CI: CI CI: :0:0 Select to Add Arrows Select to Add Arrows H H Cl CI: CI CI: Select to Add Arrows Select to Add Arrows H :CI: Alarrow_forwardI I H :0: Submit Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. 0:0 :0: CI ΑΙ :CI: :CI: :0: CI Select to Add Arrows Select to Add Arrows cl. :0: Cl © ハ CI:: CI H CO Select to Add Arrows Select to Add Arrows 10: AI ::arrow_forwardOrder the following compounds from slowest to fastest in a nucleophilic acyl substitution reaction. ii 요 OB D A E C OCE Darrow_forwardI need the most help figuring out how to find [I^-] mol/ L, [S2O8^2-] mol/L. 1st and 2nd Blank columns.arrow_forwardCan someone help me whats the issue?arrow_forwarda. The change in the Gibbs energy of a certain constant pressure process is found to fit the expression: AG-85.1 J mol −1 +36.5 J mol ¹K-1 × T A. Calculate the value of AS for the process. B. Next, use the Gibbs-Helmholtz equation: (a(AG/T)) ΔΗ - T2 to calculate the value of AH for the process.arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License