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Activation: R CH2 CH2 CO 2
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CoA ATP R CH2 CH2 C( O) SCoA
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Oxidation: R CH2 CH2 C( O) SCoA FAD R CH CH C( O) SCoA FADH2 Hydration: R CH CH C( O) SCoA H2O R CH(OH) CH2 C( O) SCoA Oxidation: R CH(OH) CH2 C( O) SCoA NAD R C( O) CH2 C( O) SCoA NADH Cleavage: R C( O) CH2 C( O) SCoA CoA R C( O) SCoA CH3C( O) SCoA What oxidation actually accomplishes is the removal of a C-2 unit as acetyl-CoA from the carboxyl end of the fatty acid This keeps happening until the fatty acid is completely converted to acetyl-CoA
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Double bond initially on odd carbon ( system): Isomerize cis-3 C C to trans-2 C C then proceed with normal oxidation 2 fewer ATPs per double bond Double bond initially on even carbon ( system): Hydrate cis-2 C C to D-3-hydroxyacyl-CoA, epimerize D-3hydroxy to L and continue normal oxidation 2 fewer ATPs per double bond Or reduce 2-trans-4-cis C C to 3-trans with NADPH; then isomerize the 3-trans to 2-trans and proceed as with normal oxidation 5 fewer ATPs per double bond
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If a fatty acid already has a double bond in it, the scheme by which the fatty acid is oxidized depends on where the double bond ends up after several of the C-2 fragments have been removed by normal oxidation With a double bond already present, the enzyme that catalyzes the first step (insertion of the double bond at C-2) gets confused when there is already a double bond at C-2 or at C-3 The fact that the double bonds in unsaturated fatty acids are invariably cis also complicates life since the double bond introduced at C-2 by the desaturating enzyme of oxidation is a trans double bond
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As the -oxidation machinery chews off 2-carbon fragments, it nibbles down to one of two possible situations depending on whether the first double bond started out at an even- or an odd-numbered carbon when counting from the carboxylate end If the double bond is on an oddnumbered carbon (as in cis 9C18:1), it is metabolized slightly differently than a fatty acid in which the unsaturation is on an even-numbered carbon (as in cis 12C18:1) If the double bond is on an odd carbon, oxidation removes 2-carbon fragments until it gets to the structure with a 3-cis double bond [R CH CH CH2 C( O) SCoA] A new double bond can t be placed between C-2 and C-3 because there s already a double bond at C-3 In this situation, the activity of an isomerase simply moves the double bond from C-3 to C-2 and at the same time makes sure that the configuration is trans From this point on, the metabolism is just like normal oxidation (hydration, oxidation, cleavage) If you re counting ATPs, these unsaturated fatty acids produce 2 fewer ATPs for each double bond since there is no FADH2 produced by putting in the double bond (see Fig 13-6) If the double bond starts out at an even carbon, oxidation runs its normal course until the structure cis-2-R CH CH C( O) SCoA is reached The rub here is that the double bond is on an OK carbon (C-2), but it s in the wrong configuration The double bonds in unsaturated fatty acids are invariably of the cis configuration, but oxidation introduces the double bond at C-2 in the trans configuration The pathway cited in most texts involves the addition of water to the 2-cis double bond to give the 3-hydroxy species just as in normal oxidation, except for a mean twist If the double bond is introduced in the trans configuration by oxidation itself, hydration gives the L-3-hydroxy fatty acyl-CoA But if the double bond is in the cis configuration, hydration gives the D-3hydroxy fatty acyl-CoA The configuration around C-3 (D vs L) might appear trivial to you, but to the enzyme that oxidizes the C-3 (C OH) to the carbonyl (C O), it s night and day The dehydrogenase won t touch the D configuration because the OH group is in the wrong place relative to the R and CoA groups To get around this problem, there s an enzyme (an epimerase) that converts the D to the L epimer The L epimer is then recognized by the dehydrogenase, and it s smooth sailing from there on Since the isomerase and epimerase don t require ATP hydrolysis, ATP counting through this pathway would show that a double bond at an even position reduces the yield of ATP by 2 (no FADH2 is formed in the first desaturation reaction) A somewhat newer pathway, which may be the real pathway in many cells, has been discovered recently This may or may not be described in your text In this pathway, the fatty acyl-CoA is metabolized
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