2. Shown below is the enol intermediate in the citrate synthase mechanism. Draw the carbanion resonance structure of this intermediate (note that the ionization of His274 might be affected). H H HC C-S-COA H His274 Asp 375 Enol intermediate
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- GTP or ATP is produced during the conversion of isocitrate into ketoglutarate succinyl CoA into succinate fumarate into malate malate into oxaloacetateDistinguishing the Mechanisms of Class I and Class I Aldolases Fructose bisphosphate aldolase in animal muscle is a class 1 aldolase, which forms a Schiff base intermediate between substrate (for example. fructose-1, 6-bisphosphate or dihydroxyacetone phosphate) and a lysine at the active site (see Figure I8.12). The chemical evidence for this intermediate conies from studies with aldolase and the reducing agent sodium borohydride, NaBH4. Incubation of the enzyme with dihydroxyacetone phosphate and NaBH4 inactivates the enzyme. Interestingly, no inactivation is observed if NabH4 is added to the enzyme in the absence of substrate. Write a mechanism that explains these observations and provides evidence for the formation of a Schiff base intermediate in the aldolase reaction.1. Shown below is the intermediate in the aldolase mechanism, after dissociation of the first product (GA-3P). Draw resonance structure of this intermediate showing the carbanion species AND the arrow movement that associated with formation of this resonance structure. CH₂OPO²- H 1 Lys-N-C || -B-H :A- H-B Covalent enzyme- enamine intermediate
- 15. Write the metabolites of the following substrates due to phase Il reactions: a. b, R R C. R R NH ΝΗ LOH 3'-phosphoadenosine-5'-phosphosulfate Enzyme S-adenosylmethionine Enzyme Acetyl-SCOAShown below is a substrate for a Trypsin. Draw the mechanism for this serine protease using the artificial substrate. Be sure to draw the catalytic triad, and show the role of the oxyanion hole. Draw the complete structure of every intermediate and product and PUSH ARROWS!!!!! Do not abbreviate structures using R and R' H₂N _N_CH. сно CH₂ CH₂ CH₂ NH d=19H₂ NH₂ O CH- H₂C HN O CH17. Omeprazole is a bioprecursor prodrug that is activated by protonation to give active metabolite that inhibits H¨,K*-ATPase covalently. By using chemical equations show activation of Omeprazole and its reaction to inhibit the H*,K*-ATPase. CH3 H3CO. s=0 H3C HNN Omeprazole OCH3 18. The following compound is an open-chain prodrug of benzodiazepines which undergo N- dealkylation to triazolam. Using chemical equations show transformation of this prodrug to triazolam. H3C H3C CH3 CH3 triazolam open-chain prodrug of triazolam
- S 1 CH₂ ✪ NH3 0=0 H₂C HN 6 NH CH₂ 'S Co A L CH₂ NH 4. Describe the role of His in the catalytic mechanism shown.1. (a) write, using structural formulas, the sequence of TCA cycle intermediates. Indicate the position of the 14C atom in each intermediate. Do not name enzymes or cofactors catalyzing the reactions. Starting with citrate formed immediately after reaction of [2-14C]acetyl-SCOA with OAA,One of the steps in psilocybin biosynthesis is the phosphorylation of 4-hydroxytryptamine By the enzyme Psik as shown below, that involves the hydrolysis of ATP. NH₂ OH HO Psik HO of A& ADP 4-hydroxytryptamine ATP norbaeocystin The standard free energy changes for each reaction is shown in the Table below. J reaction 4-hydroxytryptamine + P₁ → norbaeocystin ATP → ADP+ Pi (b) What is the equilibrium constant at 37 °C? AG 27.7 kJ/mol -32.2 kJ/mol (a) Write the net reaction. What is the standard free energy change for the net reaction? (c) In the cell, the concentration of ATP is 3.1 mM, the concentration of P; Is 5.90 mM, and the Concentration of ADP is 220 μM. What will AG Be if the concentration of norbaeocystin Is always kept at 1/100 of the concentration of 4-hydroxytryptamine?
- His388 Glu357 His388 Glu357 Ring opening Proton HO HO abstraction HO но- G6P He NH- NH His388 His388 His388 Glu357 Glu357 Glu357 HO но HO но- но OH cis-enediol F6P Ring closure intermediate OH Describe the mechanism shown above for phosphoglucose isomerase. Describe the chemistry of each step • How the enzyme appears or might facilitate the chemistry How the enzyme increases the reaction rate.8. The enzyme thiolase catalyzes one step in the ß-oxidation of saturated fats. One portion of the mechanism for this reaction is shown below. Describe the catalytic mechanism at work. (Note: "SCOA" is shorthand for the compound Acetyl-CoA) RCOCH₂COSCoA + HSCOA → H3C₂OSC0A + RCOSCOA HN NH CH₂ NH CH₂ CH₂ FS Grease NH3 H-SCO A NH CH2 CH₂ NH3 S Co A CH₂ NH 1 3 H-SCO A H3C SCO A NH3 a h-SCOA R-C S Co A CH₂ CH₂ C H₂ 0=0 HN NH + NH3 H₂C HN CH₂ NH CH₂ CH₂ 2 S Co A CH₂ NH NHCompound A below is a key intermediate in the synthesis of keto-myo-inositol B. Suggest a synthetic route for the preparation of A from D-glucose C giving structures for all of the intermediates in your scheme. Ph3CO. Но, HO HO HO, HO 'HO. ОН ОН Ph CH3 А В
