203f05_final_key

203f05_final_key - Chemistry 203 Lg (Fall 2005) FINAL EXAM...

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Unformatted text preview: Chemistry 203 Lg (Fall 2005) FINAL EXAM Last Name: 14 g: [A (4 Tuesday Dec. 13, 2005 First Name: I ' 8:00 a.m.-10:00 a.m. USC 1.1). # Q Q (L (2 2L- Professor Charles E. McKenna T.A: KQQ é _, Professor Amy M. Barrios 9 INITIAL OF LAST NAME Please do not open this exam until you are told to do so. Write legibly to avoid confusion. GOOD LUCK ! ! I will observe the rules of Acadeié'c integrity while taking this exam. Student Signature (1) Secondary protein structure consists of: - The amino acid sequence of the protein 6 Alpha helices and beta sheets — Folding of helices and sheets to form active sites - Protein-protein interactions (2) AIDS—linked opportunistic infections include: — Karposi’s Sarcoma — Pneumonia — Candida 9 All of the above (3) The compound shown is an example of a drug first discovered by: - The impetus given to anti-viral research in the 1990s 0 — Random screenin of man corn ounds g y P R,C\NH Q Serendipity (chance discovery) — Analogy with the structure of another AIDS drug (4) The compound shown contains which functional groups: G A lactam ring and a thioether — An amide and an ester — A benzene ring and an amine —— A carboxylic acid and an alcohol (5) Anthrax is: — Caused by a virus — A new disease first appearing in 2001 — Highly contagious G Caused by a bacterium (6) A cell membrane: — Has a polar hydrophilic interior — Is a barrier to all non—polar molecules — Always freely passes ions like Na+ or Cl Q Has a hydrophilic surface (7, “pH” is defined as: — minus the log [H*] in water — 10'7 M [I-I+] in water - grams H+ per liter of water —- acidic if its value is above 7 in water (8) An amino acid has equilibria in water (R = CH3): + - mgr—curacy = «moo. . w (1) 9K. . 4 +Hw—can—oo; —--.____ W 4- H‘ (2) PK! ' 10 At pH = 2, the average total charge of the amino acid is: 0 +1 — O — —1 — Cannot be determined (9) In a molecule where a boron atom has 3 things bound to it (for example, BF3), what would the optimal F—B-F angles be? _. 90° — 104° 6) 120° — 180° (10) Which ion has an octet of electrons in its outer shell? O M g2+ _ 82+ — Ar“ 11) Which definition below is IN CORRECT ? @ Lipophilic = water loving — Non-polar covalent bond = bond between two atoms of the same element — Electronegative = element that readily accepts an electron — Chiral = a compound not superimposable on its mirror image (12) Which metal is the most electropositive and will react the most violently with water? — Li — Na — K ORb (13) Consider how acetylsalicylic acid (aspirin), a drug with a pKa of 3.5, would partition between layers of octanol and water at different pHs. At which pH would most of the aspirin partition into the octanol layer? — 10 Q 1 ./”‘T — None of the above (14) Which of the following bonds shown is the most polar covalent bond? H3C—F — H3C—Cl — H3 — H3C—SH (15) How do vaccines trigger an immune response? — A vaccine can consist of genetically altered or weakened viruses that reproduce in the body to produce an immune response — Vaccines can be designed to help the immune system recognize toxins produced by bacteria or viruses — Some vaccines consist of pieces of viruses that can be recognized by the immune system (2 All of the above statements are true (16) A “codon” consists of: 0 Three DNA bases — Alpha helices and beta sheets — A mutation in the viral genome — 4x4x4 = 64 symbols (17) HIV is called a retrovirus because: — It enters the cell “backwards” —— It contains ancient mutations in its DNA - It has been reproduced in the lab through reh‘osynthetic analysis Q Its genome consists of RNA which is converted to DNA before expression (18) Which of the following equations best describes Gibb’s free energy: — AG = TAH - AS — AG = TAH + TAS a AG=AH-TAS — AG=AH+TAS (19) Which of the following drug molecules has ONLY TWO chiral carbons? H HN/“j/ o H ‘ H 0> CAN 0 OH """ "m 0 HE,“ mahH H : O H 5‘: N3 aspirin pseudoephedrine ecstasy AZT — aspirin Q pseudoephedrine — ecstasy — AZT (20) A serious side-effect of some recent AIDS drugs is: - coronary heart disease - abdominal fat deposits - lipoatrophy 9 all of the above (21) HAART stands for: — Human Anti-AIDS Retroviral 9 Highly Active Anti-Retroviral Therapy — Humans Against Animal Research on Toxicity — Honduran-American AIDS Research Training (22) Dr. Khalsa emphasized that the rapidity in progression to AIDS can be predicted by a patient’s: — CD4 (T-cell) count (higher count, slower progression) — CD4 (T-cell) count (higher count, faster progression) — Viral load (higher count, slower progression) 6 Viral load (higher count, faster progression) (23) A vaccine to prevent HIV infection has proven elusive in part because: - DNA viruses have a much higher rate of mutation than RNA viruses — HIV virus infecting the body is found solely in T—cells — HIV has a lower rate of mutation than typical bacteria 9 HIV targets the immune system (24) The ELISA “AIDS test” detects: {—9 An antibody to HIV — An HIV antigen — HIV DNA - HIV RNA (25) The picture shown illustrates: — ELISA test results —_ DNA Viral Load test result 0 Western Blot test results —— RNA Viral Load test results (26) Suppose among 1,000,000 persons, 5,000 are HIV+. One takes an “AIDS” test that is 99% accurate (1% false positives) and gets a positive result. The chance this person is really positive is about: — 1% Slow + G ,0 006 n+1; — 67% / w ~+ — 99% "7’ (27) In another group of 1,000,000 persons, 100,000 are HIV+. One person tests negative: the test gives 0.1% false negatives. The chance this person is really positive is now about: _ 0.001% 5 ' ‘07 _ “M Z [(14 CD 0.01% ' T's ' — 1% 9W“ 10% 10' . .12. T (+ (28) The compound shown on the left, L—Dopa — Is uncharged at physiological pH :O/ck an,” ck Q Is a prodrug of dopamine, shown at right i" :O/ r: — Is the drug formed from dopamine mum — Cannot be transported across the blood—brain barrier (29) Key difference between Phase 11, Phase III clinical trials of an AIDS drug: — Phase III, larger patient base, looking for both efficacy and toxicity — Phase 11, looking for toxicity only — Phase III, looking for efficacy only -— Phase II, looking for toxicity in healthy patients (30) The first step in HIV infection of a cell: — HIV RT copies viral RNA to DNA — HIV protease cleaves polyprotein to viral enzymes — Host cell synthesizes viral RNA and viral proteins 0 HIV gp120 recognizes host cell CD4 protein (31) The active form of AZT is — AZT monophosphate — AZT diphosphate a AZT triphosphate — All of the above 25%, 90% — 0.5%, 50% fi) The relative risks for HIV infection perinatally, and via HIV+ blood transfusion, are about: — 50%, 50% — 0.5%, 5% (33) T—20, One of the newest AIDS drugs used in the clinic belongs the drug class: —— Protease inhibitors — NNRTIs _ NtRTIs 0 Membrane fusion inhibitors (34) If someone were immunized against HIV, which type of test might give a “positive” result? —- Viral RNA only G ELIZA only - Both viral DNA and RNA — Both ELIZA and Western blot (35) Based on their common structural elements, the drugs shown are probably: G Protease inhibitors "’W o H o /N "x" NNNAo/TB >——< I l H o /= on " / s pn " — Non—nucleoside RT inhibitors W Q o s o NHtBu Ho‘ i A )\/\ cwso‘fin N N H H . n l u m — NUCICOSlde RT inhibitors H mm Q — Nucleotide RT inhibitors 0 o S o\ N 'memvdbtmmodmoofly (36) The drug shown is: —— Nevirapine O RU-486 — Sequanivir —— Penicillin (37) Characteristics of a Phase I clinical trial : - Double-blind — No pharmacokinetics are done -— Most of the participants in the trial suffer from the target disease 0 About 20-80 participants (38) IND vs. NDA : — NDA means FDA allows a clinical trial — IND is secured after clinical trials, permission to market drug — NDA cancels any existing patents 9 IND includes animal toxicology, but not human toxicology data (39) The first anti—syphilis drug, an arsenical compound, was discovered by: - Koch in the 1890’s — Fleming in the 1920’s Q Ehrlich in the 1900’s — Sheehan in the 1950’s (40) The primary source of “R & E” research funding to universities in biology and medicine is: - Small start-up companies -— Large drug companies — National Science Foundation (NSF) National Institutes of Health (NIH) (41) Concerning the Partition Coefficient, P: Hydrophobic drugs dissolve better in water than octanol Q P = conc(drug) in octanol/conc(drug) in water — Hydrophilic drugs dissolve better in octanol than water None of the above is true (42) Polar or ionic drugs: — Are more readily absorbed in the gut than non-polar drugs — Cross cell membranes more easily than non-polar drugs — Are often prodrug forms of non—polar drugs a None of the above is true 10 (45) © (46) C?) In a QSAR study, what is plotted against what? l/C vs. l/P Log l/C vs. log P Log C vs. log UP 1/ C vs. log P In a large group of 500 HIV+ people, the average viral load was 200 units with a standard deviation (0) i 25. Use the appropriate table on p. 14 to estimate the probability of a patient Olgag/Singaviral load of 150 or lower. Answerzp= thW» 0.01 ’2 =lX«,u//<7~ " 57/35“ v 2" QTM 0.02 I) M 0-62 0.08 Oven/1445253 m/t:2cr—+ 51/4 1’, ml/ - a... r/ M/W/v-HN" *2 “9 M J Use the appropriate table on p. 14 to solve the following problem: in a drug trial, we need to be 99.0% sure that the effect of a drug is real in order to proceed with development. Assume a sample std. deviation of 9.80, a control group mean = 10 viruses/test, and a drug group mean of only 5 viruses per test. What is the minimum number of patients needed to . . . / satlsfy the 99.0% crlterion? , J. . 7 i /- -> f 0 0 ’ 1 _x’)/.r>t‘ 4):; z: 60 f ’3‘ ’l7 M “If M :44 é 24 5 4'10 ~—) ‘6 lo 57 6 47° ~55? 5" 27 'Z-ro 3 .1 l . 15? ~ ' c r 6 “‘ /z 4/: 4; ~z"h’ ' z 2, go 1/7 ~ /-2 0.3 A small amount of a drug is added to an enzyme, and we analyze the effect using kinetics (Lineweaver-Burk plot). Vmx is unchanged but Km is increased. This suggests that the drug inhibits this enzyme: Irreversibly and competitively Reversibly and non—competitively Competitively Irreversibly 11 (47) The difference between pharmacokinetics (PK) and pharmacodynamics (PD): (9 PK measures distribution of ingested drug in different parts of the body - PK measures how well a drug works against a disease (e. g. virus) — PD measures distribution of ingested drug in different parts of the body — PD measures oral bioavailability of a drug (48) The picture shows, within a protein: - A Van der Waals (weak like-like) bond formation within a protein - Formation of a peptide bond within a protein — An electrostatic bond 0 Formation of a covalent Cys-Cys bond within a protein (49) A drug that decreases “viral load” by “3 logs” has decreased the amount of virus by: — 3 — 10 — 300 a 1,000 (50) I add more enzyme E to an enzyme—catalyzed reaction and redo its kinetics. Result: — Vm is unchanged V M 2 60 96’ 9 Vm is increased ~ Km is increased K [MG] 3” j — Km is decreased “’9 W / DOUBLE BONUS QUESTION a) For up to 4 points, give four examples of ethical dilemmas posed by the phenomenon of AIDS discussed in class. gwfl ../ u M / J l 7» \ (iv) b) For up to 2 points, name the co-discoverers of HIV/AIDS 64M; — Manta? mew c) For up to 2 points, give either the generic name of two different AIDS anti-HIV drugs currently used in the clinic; or else draw the structure of m o_n_§ drug correctly. Exceptions: any drug name or structure already used in this exam. \Dr, (Ll/J43 W- (#LLK) W 0: WWW‘M we V M A/Zw 45¢ 22/, 13 Reference Page 1 of 2 (Please Detach) Tell. 11.! P01000100. 901m: of 1110 standard normal 01511101111011 AREA 10 RIGHT Z SCJRE l.ll b.56168 I.UI5 2.5756} I.l1 2.32636 I.U2 2.U5376 U.U25 1.96039 3.!) 1.85U79 I.Ub 1.75U69 I.U5 1.6hh55 U.U6 1.55h77 U.G7 1.57579 I.UB 1.hl5l7 D.U9 1.}“076 H.1fl 1.28155 U.11 1.22653 U.12 1.17k99 9.13 1.12639 0.1L 1.38U32 U.15 1.!36103 U.15 0.99hk6 “.17 U.95‘41’7 U.18 H.91537 H.19 U.B7790 3.2l U.Bh152 9.21 U-BUSAZ U.22 H.77219 H.23 H.73885 7.2L H.7l63l H.25 I.E7hh9 H.26 U-6h335 « H.27 H.61281 U.26 U-SBZBh 0.29 H.55335 t= (M - X)/S/(\/N) Note that in this equation we are taking ‘X’ as ‘x-bar’, the sample mean value. Tobi-11.. Percentage now: to: the 1 01017101111011 1 0:111 2 2920 3 2363 1 2132 5 2.015 5 1w 7 1155 a 1880 9 1m 10 1012 2 . . 11 1 790 2. . . 12 1 782 2179 2.001 3.055 1:1 1771 2,100 2050 3.012 14 1 751 2 145 2 024 2 977 '5 1 753 2.131 2002 2907 10 1 74a . 2120 255:1 2.921 :7 1.700 I 2.110 2.507 2.” 1s 1 73¢ 1 2.101 2.552 20711 19 1729 I 2.093 25:19 2.301 20 1725 1 2.000 1.523 2345 21 1 721 1 20m 2.518 2831 22 1 717 ‘ 2.074 2.503 2319 23 1 71.1 I 2.000 2500 2.007 24 1 711 1 2054 2492 2797 25 1 703 2000 2.105 2 707 25 1.705 2050 2479 2779 27 1703 2.052 2173 2.771 211 1 701 2043 2,407 2702 29 1099 2045 1 2.402 2750 :10 1 e127 2012 l 2057 1 2 750 40 1004 I 2021 2.423 ' 2704 so 1671 1 2000 2390 2000 For Iugcr value: 01 v [rut I u I z 51:ch and an the 11-min"! normal 131210 14 Reference Page 2 of 2 (Please Detach) .o as uflanufl .,.* LI . ‘ cl ( cl cl ( ) . cl cl ( \l 5 cl 1 ( ) C cl 1 ( ,. 3 cl 1| ( (119) (120) (121) (156) momma) (157)115.) (15.) (1”) (1.1) (102).}103) (1“) (1“) (1“) (167) (16.) v7.v__ (122) (133) (130025)}13‘} SUPER- ACTINIDES 15 ...
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203f05_final_key - Chemistry 203 Lg (Fall 2005) FINAL EXAM...

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