One of the key components in fatty acid synthesis is acetoacetyl‑ACP, which is formed from a Claisen condensation of a fatty acid thioester (acetyl synthase, simplified here) with the enolate formed from the decarboxylation of malonyl ACP. The given steps show the first round of this elongation. Draw a curved arrow mechanism to show how these reactions give acetoacetyl‑ACP.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 30MP: One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to...
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One of the key components in fatty acid synthesis is acetoacetyl‑ACP, which is formed from a Claisen condensation of a fatty acid thioester (acetyl synthase, simplified here) with the enolate formed from the decarboxylation of malonyl ACP. The given steps show the first round of this elongation. Draw a curved arrow mechanism to show how these reactions give acetoacetyl‑ACP.

acetyl synthase
acetyl
synthase cO2
:0:
:0:
R,S°
R,S
malonyl ACP
(R' = ACP)
:0:
:0:
:S
`R
'R
R,S°
R,S
acetoacetyl ACP
:S:
Transcribed Image Text:acetyl synthase acetyl synthase cO2 :0: :0: R,S° R,S malonyl ACP (R' = ACP) :0: :0: :S `R 'R R,S° R,S acetoacetyl ACP :S:
Step 1: Draw curved arrows to show the
Step 2: Draw curved arrows to show formation of the
decarboxylation step.
tetrahedral intermediate.
Select Draw Rings Groups More
Erase
Select Draw Rings Groups More
Erase
C
H
S
H
S
:o :
R1
R1
:o :
Step 3: Draw curved arrows to show collapse of the
tetrahedral intermediate.
Select Draw Rings Groups More
Erase
H
S
:o :
R1
21日
Transcribed Image Text:Step 1: Draw curved arrows to show the Step 2: Draw curved arrows to show formation of the decarboxylation step. tetrahedral intermediate. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase C H S H S :o : R1 R1 :o : Step 3: Draw curved arrows to show collapse of the tetrahedral intermediate. Select Draw Rings Groups More Erase H S :o : R1 21日
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