Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 27.SE, Problem 30AP
Assume that acetyl CoA containing a 14C isotopic label in the carboxyl carbon atom is used as starting material for the biosynthesis of mevalonate, as shown in Figure 27-7. At what positions in mevalonate would the isotopic label appear?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
synthesis of suocybin
NH₂
-OH
L-Tryptophan, 7
OH
NH2
NH2
PsiD
-CO₂
Tryptamine, 6
(PsiH) [O]
NH2
NH₂
OH
-OH
HO
PsiD
PsiK
-CO₂
H
4-hydroxy-
ATP
ADP
H
tryptamine, 8
Norbaeocystin, 9
H
4-hydroxy-L-
Tryptophan, 11
SAM
PsiM)
SAH
HN
OH
O=P.
O=P-O
HO
PsiM
PsiK
OH
ADP
ATP
Psilocin, 2
SAH SAM
Psilocybin, 1
Baeocystin, 10
Provide a synthesis pathway to get the product
Lysine catabolism begins with reductive amination of a-ketoglutarate to give saccharopine in a multistep process.
Draw curved arrows to show the movement of electrons in this step of the reaction mechanism.
Arrow-pushing Instructions
7
COO
H NH3
COO
OOC
B:
COO
H NH3
COO
BH+
Chapter 27 Solutions
Organic Chemistry
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Indicate what role DMAP plays in the reaction. Indicate the structure of three reagents that can activate the carboxyl group under these conditionsarrow_forward1 Norepinephrine can be metabolized to the following metabolite in two steps as shown below. What might be the enzymes (in the correct order) responsible for these biotransformations? но но но HN -OH но- но но Он OH OH norepinephrine COMT / MAO MAO / Cyp450 MAO / Aldehyde dehydrogenase Сур450 / МАОarrow_forwardWhich of the following substituent is an ortho/para-directing deactivator? a amino group b halogen group c phenyl group d carboxyl grouparrow_forward
- rivatives: Nucleophilic Acyl Substitution Reactions - EOC O C-O [References] 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. H-C-OH ATP ADP CH₂OPO32- 3-phosphoglycerate 0= OPO32- C H-C-OH CH₂OPO32 1,3-bisphosphoglycerate Enz-SH PO43- O= C S-Enz H-C-OH CH₂OPO3² (Enzyme-bound thioester) NADH/H+ O=C NAD*, Enz-SH H H-C-OH CH₂OPO3²- glyceraldehyde 3-phosphate Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate. To simplify the drawing process, substitute the structure below for the enzyme-bound thioester. S-CH3 substitute for the CH2CH3 enzyme-bound thioester You do not have to consider stereochemistry. • You do not have…arrow_forwardH NH3 H₂N CO₂ Lysine CO₂ a-ketoglutarate NADPH/H* H H NH3* NADPH CO₂ Saccharopine The first step in the biological degradation of lysine is reductive amination with a-ketoglutarate to give saccharopine. Nicotinamide adenine dinucleotide phosphate (NADPH), a relative of NADH, is the reducing agent. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions H₂N H NH3+ CO₂ H-A CO₂ OH *H3N H :A CO₂ جائےarrow_forwardSHOW/IDENTIFY the arrow pushing mechanism in at least 4 steps. CH,OPO?- | 3* C=0 2 HO-CH2 1 CH,OPO | 1 C=0 2 Dihydroxyacetone phosphate (DHAP) Но—С H 3 aldolase + Н—С-—ОН H Н-С-—ОН 15 CH-ОРО 6. Н—С—ОН CH,OPO Fructose- 1,6-bisphosphate (FBP) Glyceraldehyde- 3-phosphate (GAP)arrow_forward
- Differentiate the molecules that are michael acceptors and the molecules that are michael donors or michael donor precursors. ilome OMe NMe₂ NMe₂ Love OMe CNarrow_forwardImidazoleglycerol‑phosphate dehydratase is an enzyme in the histine biosynthesis pathway. It catalyzes the E1 dehydration of D‑erthyro‑imidazole‑glycerol phosphate to imidazole acetol‑phosphate. This is a rare example of a biological E1 reaction, as most biological elimination reactions occur through E1cB instead. In this reaction, D‑erthyro‑imidazole‑glycerol phosphate is first protonated to form a good leaving group. Then, the leaving group is ejected to form the resonance‑stabilized carbocation shown. Draw curved arrows forming the most stable resonance structure to explain why this reaction goes through an E1 mechanism. Draw curved arrows to form the most stable resonance structure.arrow_forwardProvide a complete arrow push mechanism for each of the following reactions.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
DIGESTER-35 | VITAMINS AND THEIR RELATED COENZYMES| GPAT | NIPER | PHARMACIST| DI; Author: GPAT DISCUSSION CENTER;https://www.youtube.com/watch?v=CGrdNYmho0s;License: Standard YouTube License, CC-BY