2-more complex molecules (fatty acyl esters) as triacylglycerols.
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1 ** Fatty acids exist in two forms:- 1-free fatty acids (unesterified) 2-more complex molecules (fatty acyl esters) as triacylglycerols. ** most tissues might use fatty acids as source of energy during prolonged fasting- except the brain that use glucose as the only source of energy. ** plasma protein albumin is used for transport of fatty acid s in blood because fatty acids are hydrophobic compounds. **fatty acids have two type : 1- saturated 2-unsaturated Without double bond Contain one or more double bond.always in cis form **fatty acid give twice amount of energy than carbohydrate. **the hydrolysis of Triacylglycerides into fatty acid required: 1- water 2- Hormone Sensitive Lipase(HSL) that is usually inactive, but in prolonged fasting it becomes active by the action of 4 hormones:- A-Glucagon B-ACTH (Adrenocorticotropic hormone) C-EP /D-NE When it becomes active it will break the ester bond between the FA and glycerol (triglycerol +3H2O HSL 3 Fatty acids + Glycerol 1 P a g e
2 **β Oxidation of Fatty Acids Fatty Acids are transported to tissues bound to albumin ** Oxidation of Fatty Acids occurs in mitochondrial matrix. Degraded by oxidation at β carbon followed by cleavage of two carbon units ** the degradation of F.A. occurs between C#2 and C#3(β carbon), forming a 2 carbon molecules in the form of Acetyl CoA and the rest remain as fatty acyl CoA ** Transport of long-chain fatty acids (LCFA) into the mitochondria: After a LCFA enters a cell, it is converted in the cytosol to its CoA derivative by long-chain fatty acyl CoA synthetase (thiokinase), " an enzyme of the outer mitochondrial membrane." Because β oxidation occurs in the mitochondrial matrix, the fatty acyl CoA must be transported across the inner mitochondrial membrane that is impermeable to CoA. Therefore, a specialized carrier transports the long-chain acyl group from the cytosol into the mitochondrial matrix, This carrier is carnitine, and this rate- limiting transport process is called the carnitine shuttle. 2 P a g e
3 Reactions of β-oxidation **now we will talk about the reaction of fatty acyl CoA. It involves 4 reactions that occur at the β carbon (C#3), the first one is converted fatty acyl CoA by oxidation (removal of 2H s from fatty acyl CoA to the FAD to produce FADH2) into Enoyl CoA that occurs by the aid of acyl CoA dehydrogenase. The second step is to converted enoyl CoA (that has a double bond between α and β carbon) into 3-hydroxy acyl CoA by adding water with help of the enzyme : Enoyl CoA hydratase. The Third step is to convert 3-hydroxy acyl CoA into 3-ketoacyl CoA. These reactions involve the removal of 2 H ions from 3-hydroxy acyl CoA to NAD+ producing : NADH + H and they are done by the help of 3- hydroxy acyl CoA dehydrogenase. Notes : * If the 2H s are removed from the 2 adjacent Carbons, they will be transferred to FAD. But, if removed from hydroxyl group,they will be transferred by NAD+. ( Rule ) ** FAD : tightly bound to the enzyme ( so electrons transfer directly from the enzyme to ETC ) NADH : It is a product that dissociate from the enzyme and transfers electrons to ETC 3 P a g e
4 P.S : These reactions are similar to some of the citric acid cycle reactions. If we remove the CoA and add COO- the compound becomes succinate then it will be converted to fumarate then to malate and finally to oxaloacetate. ** the last step is the cleavage of the bond between the α and β carbons by a type of reactions called : thiolysis, its called thiolysis because the cleavage occurs by adding SH group from CoA. Thiolysis produce acetyl CoA + fatty acyl CoA, these reactions are done by an enzyme called : 3 ketoacyl CoA thiolase ** The result from any cycle of β oxidation reactions is the shortening of the Fatty acid by 2 carbons. And the cycle returns back. 4 P a g e
5 Note : the produced acyl CoA ( by thiolysis) is already activated. ( so we need activation just once; in the beginning of the whole reaction ) Energy Yield from FA Oxidation If we have these fatty acid structure CH3-(CH2)14-CO-CoA what about it??? 1- How many carbons does it contain? 16 C s 2- How many rounds of β oxidation do we need to cleave a FA with 16 C s?? ** round means cycle which means the 4 reactions we've talked about. Now, every cycle cleaves 2 C, so if we have 16C we need 7 cycles (not 8 cycle be careful ) because after 6 cycles (12C) 4 C remain in the chain (the FA with 4C is called butyric acid ) and when cleavage happens it will produce 2 Acetyl CoA. So we will produce 8 Acetyl CoA after 7 cycles. What about NADH & FADH2? It also produces : 7NADH + 7 FADH2: **Summary of the energy yield from the oxidation of palmitoyl CoA (16 carbons) : 5 P a g e
6 ** while Activation of the Acid consumes 2 ATP a Net of 129 ATP moles per mole of C16 Fatty Acid are produced by the oxidation process. ** This amount of ATP is very high in contrast of carbohydrate. so, to have a better Idea, we should calculate the amount of ATP per gram of glucose and fatty acid For glu: 180 g 38 ATP 1g x ATP X=0.21 ATP\g FOR palmitoyl CoA 256g 129ATP 1g x ATP X= 0.5 ATP\g Conclusion : the amount of ATP produced from 1 g of F.A twice the amount of carbohydrate. *in the exam the dr :call you how many ATP produce from NADH(3 OR 2.5) Carnitine **Its name indicates that it contains an amino group which comes from an amino acid. Function of carnitine: 1-transfer of acyl group across the mitochondrial membrane. (Export of branched chain acyl groups from mitochondria) 2-Excretion of acyl groups that cannot be metabolized in the body 6 P a g e
7 But the main function is to transport long chain fatty acyls across inner mitochondrial membrane. **It happens due to: Carnitine Deficiency 1- liver disease the site of synthesis. 2- malnutrition because it is synthesized from A.A. 3- Increase requirement ( like in pregnancy ). 4- Primary congenital Deficiencies" not secondary " **Dr Faisal mentioned that : secondary means acquired not born with the baby. 5- decrease uptake from the cells and decrease reabsorption from renal tubules..**the result: Ability to use FA as a fuel e.g muscle Accumulation of F.A and branched Acyl groups in cells **Our muscles use FA as one of the the primary sources of energy after prolonged fasting, and as a result for Deficiencies > muscle pain and weakness, and increased demand for glucose rise up, which might lead to hypoglycemia and a decreased amount of glucose transported to the brain. * Carnitine Deficiency is very rare but who knows, you might see a baby suffering from this case in future!! ** we have Carnitine sold in Pharmacies 7 P a g e
8 Oxidation of unsaturated F.A( Oleic Acid) **( Oleic Acid) : is a mono unsaturated fatty acid composed of 18 C with a double bond between C9 and C10, and it is written in short form as : 18:Δ9 *The unsaturated F.A oxidation uses MOST of the enzymes used in β oxidation of saturated F. A. **CH3 (CH2)7-CH = CH (CH2)7-CO~CoA(Oleic acid) **SO after 3 rounds (cycles) of β oxidation of oleic acid,we remove 6C s so the new site of the double becomes at carbon#3 At the end of 3 cycles the results are: 1-3 Acetyl CoA 2-3NADH 3-3FADH2 **CH3 (CH2)7-CH = CH CH2-CO~CoA 12:cis Δ3 If the oxidation process continues as usual, we will have a double bond between C#2 and C#3, BUT this is not possible. Because having a double bond between C3 andc4 prevents the formation of another double bond between C2 and C3, the ENZYME CAN T DO THAT. ** so the solution is to shift the double bond between C3 and C4 to C2 and C3 WITH THE HELP OF ISOMERASE ENZYME. And as a consequence, this will convert the type of bond from cis to trans. SO the product is similar to the product of acyl CoA dehydrogenase, so the process continues as if it is a saturated F.A. Oxidation of Unsaturated F.A: Linoleic Acid *Linoleic acid contains 18C s with 2 double bonds after C9 and C12(18:Δ9,12) **AFTER 3 Cycles of β oxidation it will produce 3acyl CoA and a new compound formed : 12:Δ3.6 (which is a F.A containing 12 carbons 8 P a g e
9 with a double bond between C3,C6). AND here is the same problem of Oleic,so we need an isomerase to shift the double bond from C3 TO C2, SO it will become 12:Δ2.6. and oxidation continues with the help of acyl CoA dehydrogenase. Removing of another Acetyl CoA will lead to the production of ( 10:Δ4) CH3-(CH2)4-CH=CH-CH2-CH2-CO-CoA Dehydrogenase (10:Δ4) CH3-(CH2)4-CH=CH-CH=CH-CO-CoA Reductase CH3-(CH2)4-CH-CH=CH-CH2-CO-CoA(10: Δ3) The product here is the same of that in the case of oleic acid, so an isomerase is needed to continue the process. ** these types of unsaturated F.A need 2 additional important enzymes :-- 1- Isomerase 2- Reductase Oxidation of FA with an odd number of carbons **usually F.A contain even number of carbons why? Because it is synthesized by adding 2carbons to an acetyl group at a time. When does the number of carbons become odd?? If we start the synthesis with a 3-carbon molecule "as propionic acid" instead of acetyl CoA; That happens in animals. **10% of our diet F.A are odd number Fatty acids. 9 P a g e
10 **suppose that we have a F.A with 15 C CH3-(CH2)13-CO~CoA After 6 cycles (remove 12 C s), the end products are : 1-6 Acetyl CoA 2- Propionyl CoA **Propionyl CoA undergoes carboxylation What is the name of the enzyme involved In this reaction? **propionyl CoA carboxylase enzyme because it regulate a carboxylation reaction, and it needs BIOTIN as a cofactor. Biotin is a carrier for CO2 ** the product is methylmalonyl CoA because it contains a methyl group **the next step is to shift the carboxyl group from the middle to the methyl group. This step is done by a MUTASE enzyme. After that we have dicarboxylic acid called succinyl CoA. We've noticed that oxidation of F.A with an odd number produces Acetyl CoA and Propionyl CoA that can be converted to succinyl CoA.(part of citric acid cycle).so it s the only part that gives an intermediate of cirtic acid The cycle. question now is: Can we produce glucose from F.A??? 10 P a g e
11 Can we produce glucose from oxidation of fatty acids? The answer is NO because converting of acetylcoa INTO PYRUVATE IS IRREVERSIBLE. But the opposite is TRUE. -** THE ONLY EXCPTION of converting of F.A INTO carbohydrate is in the case of the odd number F.A but not all of them, it only true when dealing with Propionyl CoA. What about a very long chain of F.A more thane 20 C-?????? Its not common,but its found in brain. The oxidation of these long chains occur or start at the peroxysome. The enzyme that catalyze these reactions is called FAD containing oxidase. The aim of these reactions is to shorten the long chain to become short enough to enter the mitochondria and continue the oxidation process. **who accepts the two hydrogens FROM FADH2??? The Oxygen does that by forming H2O OR H2O2. "that happens because peroxysome is not equipped have ETC" Alpha (α) oxidation ** this process occurs at the site of α carbon (c#2). ** the main Feature of F.A oxidized by this process that it is branching at the β carbon(contains a methyl group at β C) **It is an unusual F.A(not Straight F.A ),BUT the question is: where does that branch come from??? ** usually, this type of fatty acids is associated with chlorophyll, SO when we consume leaves,we will absorb this type of F.A. 11 P a g e
12 ** HOW can our body deal with the branching F.A?? ** β oxidation cannot be used because methyl group is already found at β carbon.the solution is to use α oxidation ** The first step of α oxidation is to add a hydroxyl (OH) group at the site of α carbon, and the second step is oxidative decarboxlation,and here the first carbon(co2) is to be removed. So, the carbon which is a β carbon becomes an α carbon What is the importance of knowing this reaction?? The importance is in the case of deficiency of the enzyme that catalyzes the α oxidation, while the result of such deficiency is the accumulation of F.A "which is a rare disease " ** It Is a congenital disease, that causes damage to CNS. How we can treat this disease??? If we find this disease in the first baby we can't do anything, but the important thing is to prevent the occurrence of this disease in the 2 nd, 3 rd,.. Babies. This way is done by dietary restriction of types of food which contain branching F.A. It's been to hard to come up with this sheet. so, sorry for any mistake and remember that our strategy "as medical students" is to study and study till it is not possible any longer, good luck ^_^ Done by : Mohammad Ibrahim Abu-Ejhesheh. special thanks to Adnan Tarawneh. Note from lec 24, 6 th page : equivalent mass consumed of fat during 12hr fasting is 60g NOT 90 Corrector JU 12 P a g e
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