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
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
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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.
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