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Organic Chemistry

Chapter 29

Organic ChemistryChapter 29

Chapter 29

Problem 29-1
HOCH2CH(OH)CH2OH + ATP ​→ ​HOCH2CH(OH)CH2OPO32− + ADP
Problem 29-2
Caprylyl CoA ​→ ​Hexanoyl CoA ​→ ​ Butyryl CoA ​→ ​2 Acetyl CoA
Problem 29-3
(a)
8 acetyl CoA; 7 passages
(b)
10 acetyl CoA; 9 passages
Problem 29-4
The dehydration is an E1cB reaction.
Problem 29-5
At C2, C4, C6, C8, and so forth
Problem 29-6
The Si face
Problem 29-7
Steps 7 and 10
Problem 29-8
Steps 1, 3: Phosphate transfers; steps 2, 5, 8: isomerizations; step 4: retro-aldol reaction; step 5: oxidation and nucleophilic acyl substitution; steps 7, 10: phosphate transfers; step 9: E1cB dehydration
Problem 29-9
C1 and C6 of glucose become  –CH3 groups; C3 and C4 become CO2.
Problem 29-10
Citrate and isocitrate
Problem 29-11
E1cB elimination of water, followed by conjugate addition
Problem 29-12
pro-R; anti geometry
Problem 29-13
The reaction occurs by two sequential nucleophilic acyl substitutions, the first by a cysteine residue in the enzyme, with phosphate as leaving group, and the second by hydride donation from NADH, with the cysteine residue as leaving group.
Problem 29-14
Initial imine formation between PMP and α-ketoglutarate is followed by double-bond rearrangement to an isomeric imine and hydrolysis.
Problem 29-15
(CH3)2CHCH2COCO2−
Problem 29-16
Asparagine
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