Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 18.5, Problem 8P
Draw the mechanism for the hydroxide-ion-catalyzed cleavage of fructose-1,6-bisphosphate.
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Chapter 18 Solutions
Essential Organic Chemistry, Global Edition
Ch. 18.1 - Prob. 1PCh. 18.2 - If H218O were used to hydrolyze lysozyme, which...Ch. 18.3 - Which of the following amino acid side chains can...Ch. 18.3 - Arginine and lysine side chains fit into trypsins...Ch. 18.4 - Which of the following amino acid side chains can...Ch. 18.4 - Prob. 6PCh. 18.5 - Prob. 7PCh. 18.5 - Draw the mechanism for the hydroxide-ion-catalyzed...Ch. 18.5 - What advantage does the enzyme gain by forming an...Ch. 18.7 - Prob. 10P
Ch. 18.7 - Prob. 11PCh. 18.8 - How many conjugated double bonds are there in a....Ch. 18.8 - Instead of adding to the 4a-position and...Ch. 18.8 - In succinate dehydrogenase, FAD is covalently...Ch. 18.8 - Prob. 15PCh. 18.9 - Acetolactate synthase is another TPP-requiring...Ch. 18.9 - Acetolactate synthase can also transfer the acyl...Ch. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 21PCh. 18.11 - Prob. 23PCh. 18.11 - Which compound is more easily decarboxylated?Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.12 - What groups are interchanged in the following...Ch. 18.13 - Why is the coenzyme called tetrahydrofolate?Ch. 18.13 - What amino acid is formed by the following...Ch. 18.13 - How do the structures of tetrahydrofolate and...Ch. 18.13 - What is the source of the methyl group in...Ch. 18 - Prob. 32PCh. 18 - Prob. 33PCh. 18 - From what vitamins are the following coenzymes...Ch. 18 - Prob. 35PCh. 18 - For each of the following reaction, name both the...Ch. 18 - Explain why serine proteases do not catalyze...Ch. 18 - Prob. 38PCh. 18 - For each of the following enzyme catalyzed...Ch. 18 - Trisephosphate isomerase (TIM) catalyzes the...Ch. 18 - Prob. 41PCh. 18 - What acyl groups have we seen transferred by...Ch. 18 - When UMP is dissolved in T2O, exchange of T for H...Ch. 18 - Prob. 44PCh. 18 - When transaminated, the three branched-chain amino...Ch. 18 - Aldolase shows no activity if it is incubated with...
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- 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.arrow_forwardFructose in its bβ - D - pyranose form accounts for the powerful sweetness of honey. The β - D - furanose form, although sweet, is not as sweet as the pyranose form. The furanose form is the more stable form. Draw the two forms and explain why it may not always be wise to cook with honey.arrow_forwardWrite the mechanism for the base-catalyzed conversion of d-fructose to d-glucose and d-mannose.arrow_forward
- Define homolysis or homolytic cleavage ?arrow_forwardModify the Haworth projection for a-D-galactose provided to draw the structure for a-D-galactose 2-phosphate. CH₂OH OH H H OH H OH H H OH :□ 5arrow_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
- Nucleosides are stable in water and in dilute base. In dilute acid, however, the glycosidic bond of a nucleoside undergoes hydrolysis to give a pentose and a heterocyclic aromatic amine base. Propose a mechanism for this acid-catalyzed hydrolysis.arrow_forward3. Propose a mechanism for the conversion from ribulose5-5phosphate to ribose-5-phosphate using the arrow formalism. This is a reaction in the pentose phosphate pathway. CH2OH с-н Ribose 5-Phosphate Isomerase c=0 H-C-OH Н-с-ОН Н-с-ОН Н-с-он Н-с-ОН H2C-OPO,2 H2C-OPO, Ribulose-5-Phosphate Ribose-5-Phosphatearrow_forwardwhat is the structure digested by and how many reducing sugars are present ОН ОН Но OH HO Но HO- OH HO, The trisaccharide pictured could be completely digested (ie into monomers) by a beta-galactosidase and an alpha-glucosidase an alpha-galactosidase and sucrase lactase and sucrase a beta-fructosidase and lactasearrow_forward
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