Exam4_key - C485 Exam IV Fall ‘10 Name ’ ‘ Legible...

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Unformatted text preview: C485 Exam IV Fall ‘10 Name ’ ‘ Legible please! 3 ‘ Do not use acronyms. Use structures whenever they are asked for, or appropriate. Your explanations should be brief. Overly lengthy answers with irrelevant or erroneous material will receive deductions. GOOD LUCK 1. (8 Pts) The compound shown below is an intermediate in the biosynthesis of cholesterol that is derived from acetate. Using the numbering system shown below for acetate, number this com ound so it is obvious how it is derived from acetate. Please draw and number aéix carbon intermediate in this pathway. OPP H30 2 1 1,6,“? ( i i p - 4H Lo 14 it 5 L . 2. (8pts) Describe the general mechanism used by cells to replace a carbonyl group with an amino group in nucleotide biosynthesis. Please use structures to illustrate your point. What are the nitrogen donors used in nucleotide biosynthesis? N I? a g. 5’. 'P—otk\ .1 (bah? ~——) Mk a , 5- 0+)“ .4 ~ mug/Lb ° +91 1- MK wk“ P-l\l/\ l N Dunors 42. ASP Célbolg\ a biosynthesis? (name(s) o tructure(s)) (aw/Via mm {, (Li/L2, MM! webfiii I «\. «an _ ~ iii; 4. (6 pts) What are thnors for synthesis of the pyrimidine base in nucleotide biosynthesis? (Name(s) or structure(s)) ’ ( V i r bib»d/L~WM&fl, Mp bit/Wis Wigwam .3 5. (12 pts) Define suicide inhibitor and give an example from pyrmidine biosynthesis (show the molecule and describe how it works— structures please). Why is such a molecule useful for anti-cancer therapy? 01 5960.496 Mbénéflor U a Sawmiegrkk’éfi {filb‘w‘ M” e“ ijaifi ‘ convene-51A 51: WM! “‘1 M 'n“¢A‘V‘J"P-J Hwka W “smalls bv QrmMon *6 K CA)qu WHOM. b {3 i g F P “m «w» "3:3 “m 0 1’ l/‘\ 0 D J Mum? r9. I ’4 i Pa , FM» maul %/ mom)»; WWA’ wt 99 "MM __ 6L cw KN/ cu TWMDT‘ CCUé ANNA/Q \ .. “LQaQ Mp¢& "T" Wv‘ nbvrvufl (L cells, Fk ‘mlm'loij’ stmikms. B‘ ,\ ) View 0“” 6. (10 pts) The carbon backbone of ceramide and sphingosines is assembled in a carbon- carbon bond forming reaction. Show the precursors for this reaction, the cofactor required for this conversion, and a mechanism for any C—C bond forming or C-C bond making events that take place in this conversion. gufm palw~:\l'n3l CoIA PL? a.) x b b c\ . “M “£40”; W5 tr \ waif“; 0% (/01. VW/pj ’K) H / a ,. v/ '6' h C‘ 7 c (“aéyw “a Mfg???” i,“ (lrl w ’ V\ i f 7. (8 Pts) There are two disorders associated with defects or misfunctions of purine 1/ degradation. What are these disorders, and indicate what the molecular basis of the 31/. defect or misfunction is (i.e. show which reaction is defective, or draw the structure of the {N z ‘5. molecule thatpis‘causing the problem). “ Q j {my art. tavmlmt WWW 0 a?th ‘ {7} WA I L [L "a ‘ btkygfilfimsl ._ i “m at ‘1 “jam/T5 ,7 amp} t t f é 7%? W6? R (on/«pt we, 2L3 9:st VllQOVVi/l»&wfi0w pf; ' t WWW «’95 NW p M)“ a n p Bruit-i /N" Am amjfxm w KHN/i‘kw {Cmm ’ V": \ n x T” ,,,,,,,,,,,,,,,,, “7 < I :3 lg ‘ A \ /\\;3 *L _ \W “~7’ i W apt: % t‘ a it tact flpfi . _ ,2 it 5‘ V H I rimm- 8% 0 pts tgtgljfi / W (2 pts.) Please name the key regulatory step in cholesterol biosynthesis. (may show enzyme or reaction) M /. (EMT/k R * r t “ i - , r , moi WMM‘W S tKWwéM/gmvl’l/WM tgmtmtwu ward/t (“Wipfim , _ ' y :2. ~ WW2N4¢U WMWW M~‘7ofilr«m) P " ' ‘ 1- dial/Ml a l wt 5“ mawwlmm ifiwmégw (2 pts) Please name a way in which the specific activity of the enzyme is modified. (6 pts) State three ways in which the concentration of this enzyme is modified. B My War Mam m out in? W l/ Mncb‘ JV) * (176‘ 37%;: tact/clap 9. (8 pts) Match the appropriate roperties in the right column with the lipoproteins in the left column. (a) chylomicron ' 7 (1) transports endogenous cholesterol (b) VLDL x ‘i esters (c) LDL ! f g” (2) transports dietary triacylglycerols (d) HDL j: l (3) transports endogenous triacylglycerols (4) is degraded by lipoprotein lipase (5) is taken up by cells Via receptor- mediated mechanisms (6) is a precursor of LDL (7) may remove cholesterol from cells 10. (12 Pts) List the three major metabolic junction molecules. List or diagram the possible fates of these molecules. / (r (“you /7 27"““4‘6‘0 \> RS)‘ p643 Pw/f I ffimlfiu:/ 5"”) gfikpgrvuaifi \ n a“); / but, ‘\ MA WK Hm w H V“ W 31k flairx‘ Mm flemM 0" L l 1. (6 Pts) Two metabolic pathways are tightly coupled to ATP synthesis. What are these pathways? Explain how this control works, and why this makes sense from a biochemical perspective. ,1. k K p t l, Mm JllW’, tamfiwfi i til/350cth (MT 0 MKW wfiCWl/Sl W’lWW WV ,’ ' WAth MW“ Mtwtalc/t/l/t 0—? : Manx/le 01/ Cl 12. (8 Pts) There are two related methods for the attachment of head groups in phospholipid biosynthesis. Show s’émfméa‘ctions and give an example of a lipid E synthesized via each pathxgay, (‘9 Wig: M" Ma r at 2 ,9 rarest—bail WM .42 ~ if ‘ ' ‘ \ ,wl‘x ‘ r 1" g: - f «.47 . ., g (’9 w ‘l M . “m ' m/\‘21 14§\%t0l ‘ "13?; ‘ 2: fr N M flat“ P + Em/HWZL lat U . ,ow , a ‘ “’0 H r ’ . , ”‘ ’ . r z a i l? i 69”? remit w gm My)"; {3 S 0 “PM " ova/«o; i ‘ \ ‘ i a w_._..a «.3 0 , a t e « ' -' r it aim/MM ‘* P , P g or Q 3: W l W MAW Pg, \ i EC 13. (10 pts) Nandrolone (structure shown below) is widely used by strength athletes. 69 What steroid(s) does this molecule mimic? There is one very obvious difference between this molecule and its natural congeners that gives nandrolone a property that the natural rp ‘ f, 3‘ steroids lack. What is this difference and what is the property? (Hint, identify one of the Ea ”” structural differences between male and female sex hormones and this may help you.) OH daisies (—462me liar/ks M< OF‘M’T’ . la.ka ‘ clamp 1%.. wnm¥ MMIZQ M Lot ax:va \W: {Shy-MS EC 14. (10 Pts) Estrogens play a key role in receptor positive breast cancer. Explain the role of this hormone in promoting growth of tumor cells. Identify two different strategies that are clinically employed to target the role of these hormones in growth of the disease. Dell (Baylor Mama)»; gunk k egmowreppwiw 61 {him AMZMW ‘l’b 9W» (Lea; 0.“ DN '9 (.iflvadao’C) M CIA-«age: rwuwr; race? 9“ “A” l as law; ‘l‘mns ccwa . 13” 0Q W QM“)? V0 4 MMwWW‘DlW Mid to W") “Wt Cdvlanwwl MUM ECl 5 (lOpts) Pyrimidine biosynthesis contains a C—N bond-forming reaction that is unusual in biosynthesis. What is this reaction and why is it so unusual? What enzymic strategy is employed to make this reaction feasible? ’0 KN)~9H IOU/JVEO J WnWJM/e “R M U963 0‘ Wfbouto . 0‘“ e,\4z,e~me\/mva as QQ! W Mons W \wmp WM? «DU / “W ( \Ov) cellar) Pr Wu lav) \AJlV‘fi QAQL MWS‘Q H_ m 4A6: («at 1 " ‘0 [ck gems cal ...
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This note was uploaded on 01/18/2012 for the course CHEM C485 taught by Professor ben burlingham during the Fall '11 term at Indiana.

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Exam4_key - C485 Exam IV Fall ‘10 Name ’ ‘ Legible...

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