ORGANIC CHEMISTRY-EBOOK>I<
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ISBN: 9781305084414
Author: McMurry
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Chapter 22.SE, Problem 30MP
One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to glucose 6-phosphate. Propose a mechanism, using acid or base catalysis as needed.
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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.
-OPO3²- Enz-SH
H-C-OH
ATP
CH₂OPO3²-
3-phosphoglycerate
O
0-0--0
O
ADP
CH₂CH3
substitute for
1,3-bisphosphoglycerate
C
H-C-OH
CH₂OPO3²-
1,3-bisphosphoglycerate
O=C
CH3-SH
substitute for
Enz-SH
H
H-C-OH
|
CH₂OPO3²-
PO4³-
O.
S-Enz
H-C-OH
glyceraldehyde 3-phosphate
Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this
intermediate.
To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH.
CH₂OPO3²-
(Enzyme-bound
thioester)
NADH/H*
NAD*,…
The rate constant for the uncatalyzed reaction of two molecules of glycine ethyl ester to form glycylglycine ethyl ester is 0.6 M-1s-1. In the presence of Co2+, the rate constant is 1.5 x 106 M-1s-1. What rate enhancement does the catalyst provide?
In the biosynthesis of aromatic amino acids, erythrose-4-phosphate undergoes electrophilic addition to
phosphoenolpyruvate (PEP). Draw the products of this step, paying particular attention to regiochemistry.
ОН
OPOH
ОН
?
Enzyme
Erythrose 4-phosphate
Phosphoenolpyruvate
(PEP)
Chapter 22 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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