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 Lys-N-C :A- #1 H H-B -B-H Covalent enzyme- enamine intermediate
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- 1. The following reaction is catalyzed by an enzyme very similar to Class I Aldolases. Write a plausible, detailed mechanism for this reaction: Fructose-6-P + Erythrose-4-P Glyceraldehyde-3-P + Sedoheptulose-7-P CH,OH CH,OH -H- H HO- OH H- H- OH Он OH ČH,OPO,? CH,OPO,2 H. OH CH,OPO,? ČH,OPO,21. (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,There is another class of aldolase enzymes known as Class II. These enzymes are found in fungi, algae, and some bacteria. This class differs for Class I in that these enzymes do not have a Lys residue associated with their active sites, but contain a divalent cation (usually Zn2+ or Fe2+) in the active site. Outline a possible mechanism for a Class II aldolase and explain the function of the metal ion in the reaction.
- Consider the mechanism of enolase, as indicated below. Which of the following correctly describes the roles of the Mg2+ as illustrated in the figure? (This is a multi- select question). Mg2+ Mg2 Enolase PO3- OH -C-C-H H OH HO H-N-H Lys 345 Glu211 2-Phosphoglycerate bound to enzyme Mg2+ Mg2 PO3- OH C-C-H OH HO H H-N*-H Lys 345 O Glu211 Enolic intermediate HOH PO3- H Phosphoenolpyruvate The metal ion (Mg2+) is helping to stabilize the extra negative charge that developed on the carboxyl group in the enolic intermediate. The metal ion (Mg2+) is serving as a general base, removing a proton in order to improve the quality of the nucleophile. The metal ion (Mg2+) is assisting in the oxidation of the carboxyl carbon through metal ion catalysis. The metal ion (Mg2+) is helping to orient the substrate properly in the active site. The metal ion (Mg2+) is accepting a proton in order to improve the quality of the leaving group.10. Procaine is known to undergo faster metabolic hydrolysis than procainamide. Give explanation. -NET2 -NEt2 HN H2N- H2N- Procainamide Procaine 11. In phase 2 metabolic transformation chloramphenicol the primary alcohol is converted to a glucuronide conjugate. Draw chemical structure of the product. Provide the name of enzyme that catalyze this metabolic reaction. он ? CHCI2 O2N- но33. Which of the following statements is true for the shown reaction? P-O-CH₂ P-O-CH₂ OH A Coo I C=O HOTHS CH₂ Coo A HỌ он D A. The reaction is catalyzed by PFK-1 B. Stimulation of the reaction eventually slows down gluconeogenesis C. Inhibition of glyceraldehyde 3-phopshate dehydrogenase leads to the accumulation of the product B D. All of the above E. None of the above OH 34. Which of the following statements is true for the shown reaction? COO™ CH₂OH HQ -℗ B CH₂ B C-o-℗ + CO₂ A. Insulin can eventually inhibit the reaction B. The reaction only take place in the presence of acetyl-CoA C. The product B is a high-energy molecule, and the next logical step is to use the energy released from B to synthesize ATP D. All of above E. None of the above
- 17. 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 triazolam1) Sketch out the schematic diagram for the enzymatic mechanism of glyceraldehyde-3-phosphate dehydrogenase (GAPDH) Please provide the structure of the functional groups of the substrate and enzyme involved in the reaction at each step (rest of the structure can be indicated as R) Indicate clearly the flow of the electrons at each step Indicate in short form the cofactor involved and the acid or basic groups of the enzyme involvedBeginning with the 1st tetrahedral intermediate, show the complete steps in chymotrypsin mechanism that occurs to form the 2nd chymotrypsin intermediate in the chymotrypsin active site. The substrate for chymotrypsin to be used is Ala-Tyr-Gly. Further, name the amino acid(s) that would be released as a result of the reactions you'd illustrated above.
- A D-aldohexose A is reduced to an optically active alditol B using NaBH, in CH,OH. A is converted by Wohl degradation to an aldopentose C, which is reduced to an optically inactive alditol D. C is converted by Wohl degradation to aldotetrose E, which is oxidized to an optically active aldaric acid F. When the two ends of aldohexose A are interconverted, a different aldohexose G is obtained. What are the structures of A-G?C Phosphoglycerate enolase coo O H-C-O-P=O CH₂OH 2-Phosphoglycerate This is a (an) d Tyrosine hydroxylase HO coo NH3 L-Tyrosine This is a (an) 0₂ coo C-O-P-C || CH₂ Phosphoenolpyruvate H₂O + HO HO L-DOPA H₂O coo NH3b) Why might the compound shown below act as a transition state analog of phosphoglucose isomerase? A drawing of the normal transition state for this enzyme is needed. HO- OH T .N -OH -OH CH₂OPO₂²-