10. (15 pts) (a) Saquinavir is an antiviral agent that acts against HIV-protease. Assess the structure in terms of Lipinski's rules and Veber's parameters (log P = 4.2; polar surface area = 167 Å). (b) Suggest five possible regions in saquinavir that might be susceptible to metabolism and identify the possible metabolite formed. N IZ || H ZI Ill Il Saquinavir I Z H H
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- (12) Calculate the pK, of dichloroacetate. Formulate the base association equilibrium for dichloroacetate. Consider the acid dissociation equilibrium: Ka = ChCHCOO- + H+ Cl2CHCOOH Ka = 2.71 · 10-11X 10 (select) v molecules of penicillinPara-aminobenzoic acid has two ionizable groups. One is a carboxylic acid that ionizes through loss of a proton thereby forming a charged para-aminobenzoic acid carboxylate anion, and the other is an amine connected to an aromatic (benzene) ring that ionizes by accepting an H+ to form a positively charged ammonium ion. The pk of the carboxylic acid is 4.9 and the pk of the amino group is 2.5. Assume that the intracellular pH within a bacterial cell is 7.0. N- H O-H H + H-N- H pK₂ = 2.5 Which of the following structures correctly depicts how most of the para-aminobenzoic acid is ionized at pH 7? A. B. O-H C. H H + H-N- H H D. H N- O-H H pK₂ = 4.9
- 011/19 CH3 HO HO CH2 HO H HO H HO HO. H OH HO" Но H. 02,00~ CH3 Но HN ZHN" CH3 explain your choices. (9) Which of the following molecules might also make a suitable resolving agent for ibuprofen? BrieflyWhat is the ratio of CATION to ANION in Drug X? [blank1] H₂C -H Fogy CH3 SO42 'N CH3 Drug X CH3NH Describe the possible interactions between the SIDE CHAINS of amino acids: I. and II.... II. and III... I. and III... 1. COO NH3* 2 HO II. COO HO NH3* COO NH3* III.10:57 Fri 27 May 5 T + 2. Using the diagrams of macromolecules write the corresponding number of each: Glycerol Phospholipid. Saturated Adenine amino acid Unsaturated protein fatty acid B- Glucose fatty acid Triphosphate ОН OH О OH NH₂ 4 2 3 C H-C-CH2-SH Н H CH₂OH OH Н H 12 1 НО 5 8 НО OH OH OH CI 0 OH OH NH, 9 13 CI 6 H HO 10 CH OH Н H 10 OH Н 14 О Н OH он OH H OH OH О O-P-O-CH, 11 7 11 0 CH OH CH2-OH Ay 0 OH ОН 21. ОН HO но- но CH,OH OH 5_ _ _ _ 15 CH₂-OH 76%
- C6H4(OH)2(aq) + H2O2(aq) → C6H4O2(aq) + 2H2O(1) hydroquinone quinone Calculate AHRXN for this reaction from the following data, CLEARLY SHOWING ALL CALCULATIONS: (i) C6H4(OH)2(aq) → C6H4O2(aq) + H2(g) AH = + 177.4 kJ (ii) H2(g) + O2(g) H2O2(aq) AH = – 191.2 kJ -> AH = – 241.8 kJ → H2O(g) → H2O(1) (ii) H2(g) + 1/2 O2(g) AH = – 43.8 kJ (iv) H2O(g) ↑ ↑ ↑ ↑Give a rational approach to drug design and drug development of oxamniquine and cimetadine. The answer should be handwritten in about 10-12 pagesOrnithine is an amino acid that is not used in the synthesis of proteins, but is an important intermediate in several metabloic pathways including the urea cycle and the synthesis of polyamines. It has a perfectly ordinary terminal amino group and terminal carboxyl group like any other amino acid (so use the pKas for those groups given on your amino acids handout), and a side chain with a single ionizable side group with a pKa of 10.3. If ornithine is placed in solution at pH 7.0, it has a net charge of +1. What would the net charge on this amino acid be if the pH of the solution was raised to pH 12.0? Please explain your reasoning.
- 9. Phosphotyrosine (shown below) has four ionizable functional groups (pK1 = 2.5, pKR1 = 2.1, pKr2 = 7.2, pK2 = 9.5). (a) Write the equilibrium equation for its four ionization forms and assign the proper pka for each ionization. DRAW the structure of phosphotyrosine in each ionization state. What is the net charge on the phosphotyrosine molecule in each ionization state? *H3N. pk2 - 9.5 .COOH pK, - 2.5 O=P-OH pKRI - 2.1 ÖH pKRI - 7.2 (b) Draw the titration curve of phosphorotyrosine and indicate each pKa and the isoelectric point (pl), indicate the molar equivalents of OH on the x-axis.(a) What is the difference between the hormones progesterone and testosterone? (b) Draw the structure of a a steroid nucleus. (c) Give the products obtained from complete base hydrolysis in the following reaction: O || CH,−O−C−(CH2)14–CH3 O CH–0–C−(CH2)14—CH3 + 3 NaOH O CH,−0–C−(CH2)14–CH321-43 Give appropriate names for the following compounds: (а) (b) (с) CH;CH,CH,CH2 -C-ci Ph CH, CH,CH-C-N-Ph (d) (e) () H. CH3CH N-ċ-Ph CH3CH,-Č-0-Ph CH3CH 0-C-Ph (g) hoonon (h) (1) CH;CH,O OCH CH, (G) (k) (1) H,C CH- C-N(CH,CH3)2 H;C O.