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The biosynthesis of fatty acids is accomplished two carbons at a time by an enzyme complex called fatty acid synthetase. The biochemical reactions involved in fatty acid synthesis are described in Special Topic G (WileyPLUS). Each of these biochemical reactions has a counter-part in synthetic reactions you have studied. Consider the biochemical reactions involved in adding each −-
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- Linoleic acid is shown below. What makes this fatty acid particularly susceptible to autoxidation? 1. The red CH bond has a low bond dissociation energy because it is doubly allylic. 2. The red CH bond has a high bond dissociation energy because it is doubly allylic. 3. The red CH bond is the most accessible to reaction with O2 because it is the least sterically crowded CH bond. 4. Both 2 and 3.arrow_forwardProstaglandins are a class of eicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax Km = mM/min mMarrow_forwardA graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. If this reaction could be accomplished using H2 and a nickel catalyst, would the product be optically active? Explain.arrow_forward
- ● Give three examples of how elimination reactions are used in drug synthesisarrow_forwardGiven the reaction of the synthesis of ethyl acetate: CH3COCH3 + Br2 + H3O+ → CH3COCH2Br + HBr + H3O+ Which is the catalyst? H3O+ CH3COCH3 CH3COCH2Br Br2arrow_forwardDigitalis is a preparation made from the dried seeds and leaves of the purple foxglove, Digitalis purpurea, a plant native to southern and central Europe and cultivated in the United States. The preparation is a mixture of several active components, including digitalin. Digi- talis is used in medicine to increase the force of myocardial contraction and as a conduction depressant to decrease heart rate (the heart pumps more forcefully but less often). HC OH H,C H CH3 H. H. (a) Describe this glycosidic bond OCH, H A (b) Draw an open-chain Fischer projection of this monosaccharide CH3 H. (e) Describe this glycosidic bond OCH, HA H. HO H) H. OH НО (d) Name this monosaccharide unit H. OH Digitalinarrow_forward
- Prostaglandins are a class of eicosanoids, fatty acid derivatives involved in a variety of important phenomena, including fever, inflammation, and pain. The first step in prostaglandin synthesis involves the conversion of the 20-carbon fatty acid arachidonic acid to PGG2 by the enzyme prostaglandin endoperoxide synthase, or cyclooxy: Ibuprofen is one of several inhibitors of cyclooxogenase used therapeutically. Arachidonic acid 20₂ 0.5 1.0 1.5 2.5 3.5 cyclooxrygenase PGG₂ JOH محمد The following kinetic data were obtained for the enzyme cyclooxygenase in the absence of any inhibitor (1), and in the presence of ibuprofen (2) at a concentration of 48 [arachidonic acid] (uM) (1) v(uM/min) (2) v(uM/min) 23.5 32.2 36.9 41.8 44.0 16.67 25.25 30.49 37.04 38.91 Ibuprofen A. Plot the data in standard Michaelis-Menten form as well as in double-reciprocal form. B. Determine Vmax and Km for the enzyme. C. Based on this limited data set, what type of inhibition does ibuprofen likely exhibit?…arrow_forwardFill in the missing product (R) а меона меон b* H*, H₂O CO₂Me CO₂Me a Na toluene bH, H₂Oarrow_forwardAcetylsalicylic acid commonly inflammation, and acts as a blood thinning agent. A group of STEM students experimented technique. The following are the initial materials for the experiment: 5.00 g of pure salicylic acid, 7.14 sulfuric acid as catalyst. After successful synthesis, the group was able to collect 5.25 grams of Aspirin. (Atomic weights: C= 12 amu; H = 1 amu; O= 16 amu; density acetic anhydride = 1.08 g/mL) known as Aspirin is used to treat fever, on the synthesis of this compound using recrystallization of acetic anhydride and 8 drops concentrated %3D Chemical reaction involved: OH C-CH3 0-C-CH3 C-OH C-CH3 CH3-C-OH C-OH Acetic anhydride Acetylsalicylic acid (C 9H8O4) Acetic Acid Salicylic acid (C7H603) (C 4H603) (C 2 H402)arrow_forward
- When 2-chloro-2-methylpropane, (CH3)3CCl, reacts with aqueous sodium hydroxide, the process is not a “concerted process”; instead a reactive intermediate, (CH3)3C+, is formed as a result of the first step of the reaction mechanism. Explain why this happens.arrow_forwardH3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3arrow_forwardCyclic forms of D-glucose: Furanose and Pyranose Recall that aldehyde and alcohol react to form hemiacetal. The O in OH acts as nucleophile, attacking the partially positive C of C=O. The H from the OH of alcohol is transferred to the O of C=O. он R R1 HO, On the other hand, ketone and alcohol also react to form hemiketal. OH R R2 R R1 HO, In glucose the OH in C-4 or C-5 can react with the C=O. If the C-4 OH reacts with the C=O the structure is a furanose (5-membered ring); if C-5 OH the product is a pyranose (6-membered ring). Furanose and pyranose are derived from cyclic ethers furan and pyran. Both furanose and pyranose have two isomers: the alpha and beta (also called anomers). Furan Pyran Furanose and pyranose form of D-glucose (note the numbering of carbon atoms) Furanose (5-membered ring) Alpha Pyranose (6-membered ring) Alpha Beta Beta 1 HO- Но H- Но H- _2 FH- H- OH FHO- H HO. но- H- но- H. Но Но H-4 H_5. FHO- FHO- H OH 6CH2OH H CH,OH CH,OH CH2OH C-1 OH is on the right Alpha-D-…arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning