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Chapter 21 Lipid Biosynthesis Multiple Choice Questions 1. Biosynthesis of fatty acids and eicosanoids Ans: E Which of the following is not required in the synthesis of fatty acids? A) B) C) D) E) Acetyl-CoA Biotin – HCO3 (CO2) Malonyl-CoA NADH 2. Biosynthesis of fatty acids and eicosanoids Ans: D 14 If malonyl-CoA is synthesized from CO2 and unlabeled acetyl-CoA, and the labeled malonate is then used for fatty acid synthesis, the final product (fatty acid) will have radioactive carbon in: A) B) C) D) E) every C. every even-numbered C-atom. every odd-numbered C-atom. no part of the molecule. only the omega-carbon atom (farthest carbon from C-1). 3. Biosynthesis of fatty acids and eicosanoids Ans: E Which one of the following statements best applies to synthesis of fatty acids in E. coli extracts? A) B) C) D) E) Acyl intermediates are thioesters of a low molecular weight protein called acyl carrier protein. – CO2 or HCO3 is essential. Reducing equivalents are provided by NADPH The ultimate source of all the carbon atoms in the fatty acid product is acetyl-CoA. All of the above are true. 4. Biosynthesis of fatty acids and eicosanoids Ans: D In comparing fatty acid biosynthesis with oxidation of fatty acids, which of the following statements is incorrect? A) A thioester derivative of crotonic acid (trans-2-butenoic acid) is an intermediate in the synthetic path, but not in the degradative path. B) A thioester derivative of D--hydroxybutyrate is an intermediate in the synthetic path, not in the degradative path. C) Fatty acid biosynthesis uses NADPH exclusively, whereas oxidation uses NAD+ exclusively. Chapter 21 Lipid Biosynthesis D) Fatty acid degradation is catalyzed by cytosolic enzymes; fatty acid synthesis by mitochondrial enzymes. E) The condensation of two moles of acetyl-CoA in the presence of a crude extract is more rapid in bicarbonate buffer than in phosphate buffer at the same pH; the cleavage of acetoacetyl-CoA proceeds equally well in either buffer. 5. Biosynthesis of fatty acids and eicosanoids Ans: E Which of the following is not true of the fatty acid synthase and the fatty acid -oxidation systems? A) B) C) D) E) A derivative of the vitamin pantothenic acid is involved. Acyl-CoA derivatives are intermediates. Double bonds are oxidized or reduced by pyridine nucleotide coenzymes. The processes occur in different cellular compartments. The processes occur in the mitochondrial matrix. 6. Biosynthesis of fatty acids and eicosanoids Ans: D The rate-limiting step in fatty acid synthesis is: A) B) C) D) E) condensation of acetyl-CoA and malonyl-CoA. formation of acetyl-CoA from acetate. formation of malonyl-CoA from malonate and coenzyme A. the reaction catalyzed by acetyl-CoA carboxylase. the reduction of the acetoacetyl group to a -hydroxybutyryl group. 7. Biosynthesis of fatty acids and eicosanoids Ans: A Which of these can be synthesized by plants but not by humans? A) B) C) D) E) 9,12 Linoleate [18:2( )] Palmitate (16:0) Phosphatidylcholine Pyruvate Stearate (18:0) 8. Biosynthesis of triacylglycerols Ans: B The biosynthesis of triacylglycerols from acetate occurs mainly in: A) B) C) D) E) animals but not in plants. humans after ingestion of excess carbohydrate. humans with low carbohydrate intake. plants but not in animals. none of the above. Chapter 21 Lipid Biosynthesis 9. Biosynthesis of triacylglycerols 2 Ans: D The synthesis of both glycerophospholipids and triacylglycerols involves: A) B) C) D) E) CDP-choline. CDP-diacylglycerol. phosphatidate phosphatase. phosphatidic acid. phosphoethanolamine. 10. Biosynthesis of triacylglycerols Ans: B Which of these statements about triacylglycerol synthesis is correct? A) B) C) D) E) Humans can store more energy in glycogen than in triacylglycerols. Insulin stimulates conversion of dietary carbohydrate into triacylglycerols. It is not a hormone-sensitive process. Mammals are unable to convert carbohydrates into triacylglycerols. Phosphatidate is not on the pathway of triacylglycerol synthesis. Short Answer Questions 11. Biosynthesis of fatty acids and eicosanoids In the conversion shown below (which occurs during fatty acid synthesis), if the compound on the left 14 were labeled with C in its middle carbon (*), where would the label be in the compound on the right? Circle the atoms that would be labeled. (Not all reactants are shown.) Ans: The compound on the right, butyryl-ACP, would be labeled in C-2 (C-1 is the acyl carbon). 12. Biosynthesis of fatty acids and eicosanoids The reaction sequence that leads to fatty acid synthesis includes (1) condensation, (2) first reduction reaction, (3) dehydration, and (4) second reduction. Show the first reduction reaction, with any required cofactors. + + Ans: -ketoacyl-ACP + NADPH + H hydroxyacyl-ACP + NADP 13. Biosynthesis of fatty acids and eicosanoids Fatty acid synthesis and fatty acid breakdown occur by similar pathways. Describe, very briefly, four ways in which the synthetic and breakdown pathways differ. Ans: Fatty acid synthesis (in any order) (1) employs NADPH as reducing agent; (2) involves an acyl group bound to a protein, ACP; (3) takes place in the cytosol of animals; (4) involves the condensation of malonyl- and acetyl-groups; (5) involves the formation of the D--hydroxyacyl Chapter 21 Lipid Biosynthesis derivative. Fatty acid breakdown (1) employs NAD+ as electron acceptor; (2) involves acyl groups bound to coenzyme A; (3) occurs in the mitochondrial matrix; (4) does not involve malonylderivatives; (5) involves the L-stereoisomer of the -hydroxyacyl derivative. 14. Biosynthesis of fatty acids and eicosanoids The synthesis of fatty acids and their breakdown by oxidation occur by separate pathways. Compare the two paths by filling in the blanks below. (Some blanks may require more than one answer.) Activating group Electron carrier coenzyme(s) Basic units added or removed Cellular location of process Synthesis oxidation —————————————————— _______________ ______________ _______________ ______________ _______________ ______________ _______________ ______________ Ans: Synthesis oxidation ———————————————————— Activating group Electron carrier coenzyme(s) Basic units added or removed Cellular location of process acyl carrier protein NADPH malonyl- and acetylcytosol in animals, chloroplast in plants CoA—SH NAD+ acetylmitochondrial matrix 15. Biosynthesis of fatty acids and eicosanoids Show the structure of each intermediate in the conversion of -hydroxybutyryl-ACP to butyryl-ACP by the fatty acid synthetase complex. Show where cofactors participate. In your first intermediate, circle the carbon atoms that are derived from malonyl-CoA. 2 Ans: -hydroxybutyryl-ACP is first dehydrated, yielding trans- -butenoyl-ACP, which is then reduced to butyryl-ACP, with NADPH as the reducing agent. (See Fig. 21-6, p. 810.) 16. Biosynthesis of fatty acids and eicosanoids Pages: 815-816 Difficulty: 2 Explain briefly why we require fats in our diets. Ans: Dietary fats provide the linoleate and linolenate that we need (for eicosanoid synthesis) but cannot synthesize.