One of the steps in fatty-acid biosynthesis is the dehydration of (R)-3-hydroxybutyryl ACP to give trans-crotonyl ACP. Does the reaction remove the pro-R or the pro-S hydrogen from C2?
Added by Lisa S.
Step 1
We are given that the starting compound is (R)-3-hydroxybutyryl ACP. This means that the hydroxyl group is on the 3rd carbon and has an R configuration. Show more…
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In step $7 \text { of fatty-acid biosynthesis (Figure } 29.5),$ dehydration of a $\beta$ -hydroxy thioester occurs to give trans-crotonyl ACP. Is the dehydration a syn elimination or an anti elimination? (EQUATION CAN'T COPY)
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How does Nature use an elimination reaction to make these important molecules? The biosynthesis of fatty acids occurs over a multi step cycle, part of which is shown below. Step 1: beta–hydroxybutyryl-ACP undergoes an elimination reaction to form an intermediate called crotonyl-ACP. Step 2: Crotonyl-ACP is reduced to butyryl-ACP, which is then converted to fatty acids. Predict the structure of crotonyl-ACP formed in Step 1. (Hint: the OH group of beta–hydroxybutyryl-ACP acts as a leaving group)
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