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1 number 21 Done by Omar Sami Corrected by حسام أبو عوض Doctor Faisal Al- Khateeb 1 P a g e
2 (Only one or two marks are allocated for this sheetin the exam). Through this lecture we are going to cover the process of Oxidation of Fatty Acids, through what we call beta oxidation. General Overview What is the main purpose of this oxidation? Well, this oxidation s goal is to produce Acetyl Co-A which enters the TCA cycle and participates in energy yielding, also, the oxidation of fatty acid yields NADH and FADH₂ which are coenzymes used in the electron transport chain. Why is it called so? It is named as such because the beta carbon of the fatty acid undergoes oxidation to a carbonyl group. Biochemistry can t be more dull, so here are the details; Every fatty acid, in order to be oxidized, must pass through these sequential steps: 1. Activation and membrane transport of free fatty acids by binding to coenzyme A (see diagram for the structure. The thiol group at the end (pink region) is the reactive group of coenzyme A). 2. Oxidation of the beta carbon to a carbonyl group. 3. Cleavage of two-carbon producing acetyl CO-A and acyl CO-A. Step 1: Activation of the Fatty acid Activation of the fatty acid (FA) occurs through joining the FA with Co-A. RCO~SCoA (Thioester bond), is a high energy bond. FA + HSCoA + ATP FA~CoA + AMP + PPi notice that this reaction is reversible because we are breaking & at the same time forming a high energy bond (the thioester bond). PPi+ H2O 2 Pi notice that the PPi is hydrolized by water to produce two inorganic phosphates. However, AMP interacts with one ATP to produce 2 ADP s through this reaction: 2 P a g e
3 AMP + ATP ADP + ADP.Because AMP (rather than ADP) is the product from the first reaction, it requires the equivalent of two ATP molecules to supply it with energy. FA + HSCoA + 2ATP FA~CoA + 2ADP + 2 Pi Enzyme involved: thiokinase (Acyl CoA Synthetase), whenever the enzyme synthetase is used, it means that ATP is needed (synthase = no ATP needed). Location: - outer mitochondrial membrane & mitochondrial matrix (for short and medium chain FA). By the end of the first step, Acyl Co-A is formed. Step 2: Transport of long chain Acyl CoA across inner mitochondrial membrane. Notice that Acyl Co-A can t pass through the inner mitochondrial membrane, so a carrier system is required Carnitine Shuttle. What does the Carnitine shuttle consist of? It consists of: Carrier molecule - Two enzymes - Membrane transport protein. You should remember that: short and medium fatty acids don t require a shuttle; they simply diffuse through the inner mitochondrial membrane. The two enzymes that are involved in Acyl Co-A transport to the inside of the mitochondria are: 3 P a g e
4 - Carnitine palmitoyl transferase 1 (Carnitine Acyl transferase 1) - Carnitine palmitoyl transferase 2 (Carnitine Acyl transferase 2) The transferase 1 enzyme attaches the carbons with Carnitine molecule, leaving the CoA in the intermembranous space. However, the transferase 2 enzyme attaches the carbons back with CoA in the mitochondrial matrix. Then, Carnitine leaves the mitochondrial matrix through a translocase back to the intermembranous space. Remember that:this shuttle is For Long chain fatty acids, and Inhibited during fatty acid synthesis, also it is not required for medium and short chain fatty acids. Let us stop here, and see where we are heading: The fatty Acyl CoA in now in the mitochondrial matrix, further beta oxidation of the activated fatty acid will lead to production of acetyl CoA, a main intermediate in the TCA cycle. Before looking at the reactions in the picture below, notice that any fatty acyl CoA that enters the mitochondrial matrix will pass through these steps: - Dehydrogenation Acyl CoA dehydrogenase. - Hydration Enoyl CoA hydratase. - Dehydrogenation 3-Hydroxyl CoA dehydrogenase. ** These steps are similar of those of Krebs cycle, just mentioned in the lecture. But what is the purpose of these Steps? The main purpose of these steps is to establish a double bond on thebeta carbon for beta Oxidation. Note: FAD cleaves 2 electrons from two Adjacent atoms. Alkane Alkene Alcohol 4 P a g e
5 Let us assume that instead of acetyl CoA in this step, we used water, what would happen? Well, instead of having a Fatty acyl CoA, we will end up with an inactivated fatty acid that requires activation, again, to be oxidized. And we keep repeating this mechanism until we end up ONLY with acetyl CoA molecules. Remember that: the bond between a fatty acid and coenzyme A is a thioester bond. : )على األغلب سؤال اإلمتحان منها ( rules Important Energy Yield from FA Oxidation: Even numbered fatty acids Each cycle causes the release of 2 carbons. number of cycles needed to degrade the fatty acid to Acetyl CoA s = (# of carbons / 2) 1 # of acetyl CoA s = the number of Carbons in the fatty acid/2. # of acetyl CoA s produced each cycle is One, except for the last cycle where the number of carbons equals 4, thus this cycle will yield two CoA s. # of NADH s & FADH₂ s is equal to the number of cycles. Eg: 16-C palmitate goes through 7 passes of the sequence, and a total of 8 acetyl CoA s are generated, 7 NADH s & 7 FADH₂ s, which make respectively 96 ATP s, 21 ATP s & 14 ATP s. Remember the question: why is it more efficient to store energy in the form of FATS not carbohydrates? Now we may have a clearer idea. Palmatic acid which has a molecular weight of 260g/mol produces 129 ATP when oxidized, while glucose, molecular weight180 g/mol, produces only 38 ATP, 3 times more ATP production though little difference in the molecular weight. 5 P a g e
6 Carnitine: Major source of Carnitine is meat, which is a muscle & thus uses FAT as a major source of energy. Other functions: - Export of branched chain acyl groups from mitochondria.. - Excretion of acyl groups that cannot be metabolized in the body. Carnitine Deficiencies Secondary deficiencies: Liver disease, malnutrition, requirements Primary (Congenital) Deficiencies: Enzyme, uptake, tubular reabsorption Ability to use FA as a fuel. Accumulation of F.A and branched Acyl groups in cells. We can evade this deficiency also by administering medium and short Fatty acid chains which don t require Carnitine. Oxidation of Unsaturated F.A Oleic Acid The fattyacidoxidation sequence just described is typical when the incoming fattyacid is saturated (having only single bonds in its carbon chain). However, most of the fattyacids in the triacylglycerols and phospholipids of animals and plants are unsaturated, having one or more double bonds. To explain the differences between this process and the oxidation of saturated fatty acids let s take the monounsaturated fatty acid Oleic acid as an example.oleic acid (18 carbons) has a double bond (cis) at carbon #9, this means that the in the 6 P a g e
7 first eight carbons no double bonds are present, so we can produce three acetyl Co-A molecules in the same way described previously with no problems at all (not 4 molecules because in each cycle three carbons are involved in the reaction, but only two leave at the end). After that we end up with the remaining part of the Oleic acid, that is 12 carbons with a double bond at carbon #3. If this same molecule was present but without the double bond the next step would be to make a double bond at carbon #2, yup, we are just 1 carbon off to having our next reactant. Simply we transfer this double bond from carbon #3 to carbon #2, this is done by the enzyme isomerase (an isomerisation reaction occurs. If there is only one reactant and only one product and both have the same molecular formula, then it is an isomerisation reaction). After that the reaction proceeds in the same way as the oxidation of saturated fatty acids. Linoleic Acid This fatty acid has two double bonds, one at carbon #9 and the other at carbon #12 (Linoleic acid has 18 carbons). Just like oleic acid, the first three cycles can go on normally with no problems at all, then we get a 12-carbon fatty acid with double bonds at carbon #3 and #6. Via an isomerase enzyme the double bond at carbon #3 is moved to carbon #2, a 4 th cycle can proceed now. The remaining fatty acid is a 10-carbon unit with a single double bond at carbon #4, a dehydrogenase enzyme forms another double bond at carbon #2, now we have conjugated double bonds. Now, a reductase enzyme removes one double bond and moves the other to carbon #3 (reduction reaction). Now an isomerase enzyme can move our double bond to carbon #2, the 5 th cycle can proceed normally producing an acetyl Co-A molecule. Now only saturated carbons remain so we can proceed with the remaining cycles normally. 7 P a g e
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