Homework Help is Here – Start Your Trial Now!
Science
Biochemistry
a) Based only on the proton affinity values, which is the least likely position for initial protonation of an ether oxygen in sucrose? b) Sketch two pathways that could follow protonation at ether oxygen B in aqueous solution and would lead to glucose and fructose. c) Figure 2 shows a simulation configuration used to study sucrose protonation at position B in an aqueous solvent. Discuss the rationale for choosing the number and location of water molecules in the model.

a) Based only on the proton affinity values, which is the least likely position for initial protonation of an ether oxygen in sucrose? b) Sketch two pathways that could follow protonation at ether oxygen B in aqueous solution and would lead to glucose and fructose. c) Figure 2 shows a simulation configuration used to study sucrose protonation at position B in an aqueous solvent. Discuss the rationale for choosing the number and location of water molecules in the model.

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
See similar textbooks
icon
Related questions
Question

4

In aqueous solution, sucrose, 3, can react to form glucose and fructose. This process is acid catalysed, beginning with ether oxygen protonation. Table 2 gives the calculated proton affinities (PAS) for the ether oxygen atoms in sucrose. Protonation at position B leads to cleavage of the C-O bond to the six membered ring, B6, or the C-O bond with the five membered ring, B5. HOH₂C OH HO OH OH₂C B C -CH₂OH OH 3 H-Q CH₂OH; HA он н HO Table 2. Calculated proton affinities for sucrose. a) Based only on the proton affinity values, which is the least likely position for initial protonation of an ether oxygen in sucrose? Position A B6 B5 C b) Sketch two pathways that could follow protonation at ether oxygen B in aqueous solution and would lead to glucose and fructose. c) Figure 2 shows a simulation configuration used to study sucrose protonation at position B in an aqueous solvent. Discuss the rationale for choosing the number and location of water molecules in the model. B Proton affinity / eV 9.11 9.23 9.34 9.43 HOH₂C C H HO OH H CH₂OH- H Figure 2. Configuration used to study sucrose protonation at ether oxygen B.
Transcribed Image Text:In aqueous solution, sucrose, 3, can react to form glucose and fructose. This process is acid catalysed, beginning with ether oxygen protonation. Table 2 gives the calculated proton affinities (PAS) for the ether oxygen atoms in sucrose. Protonation at position B leads to cleavage of the C-O bond to the six membered ring, B6, or the C-O bond with the five membered ring, B5. HOH₂C OH HO OH OH₂C B C -CH₂OH OH 3 H-Q CH₂OH; HA он н HO Table 2. Calculated proton affinities for sucrose. a) Based only on the proton affinity values, which is the least likely position for initial protonation of an ether oxygen in sucrose? Position A B6 B5 C b) Sketch two pathways that could follow protonation at ether oxygen B in aqueous solution and would lead to glucose and fructose. c) Figure 2 shows a simulation configuration used to study sucrose protonation at position B in an aqueous solvent. Discuss the rationale for choosing the number and location of water molecules in the model. B Proton affinity / eV 9.11 9.23 9.34 9.43 HOH₂C C H HO OH H CH₂OH- H Figure 2. Configuration used to study sucrose protonation at ether oxygen B.
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Recommended textbooks for you
Biochemistry
Biochemistry
Biochemistry
ISBN:
9781319114671
Author:
Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:
W. H. Freeman
Lehninger Principles of Biochemistry
Lehninger Principles of Biochemistry
Biochemistry
ISBN:
9781464126116
Author:
David L. Nelson, Michael M. Cox
Publisher:
W. H. Freeman
Fundamentals of Biochemistry: Life at the Molecul…
Fundamentals of Biochemistry: Life at the Molecul…
Biochemistry
ISBN:
9781118918401
Author:
Donald Voet, Judith G. Voet, Charlotte W. Pratt
Publisher:
WILEY
Biochemistry
Biochemistry
Biochemistry
ISBN:
9781305961135
Author:
Mary K. Campbell, Shawn O. Farrell, Owen M. McDougal
Publisher:
Cengage Learning
Biochemistry
Biochemistry
Biochemistry
ISBN:
9781305577206
Author:
Reginald H. Garrett, Charles M. Grisham
Publisher:
Cengage Learning
Fundamentals of General, Organic, and Biological …
Fundamentals of General, Organic, and Biological …
Biochemistry
ISBN:
9780134015187
Author:
John E. McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher:
PEARSON
SEE MORE TEXTBOOKS