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Chapter 21 Lipid Biosynthesis

Multiple Choice Questions


1. Biosynthesis of fatty acids and eicosanoids Pages: 787-78 !ifficulty: 2 "ns: # Which of the following is not required in the synthesis of fatty acids?

A) B) C) !) #)

Acetyl-CoA Biotin HCO3 (CO ) "alonyl-CoA $A!H

2. Biosynthesis of fatty acids and eicosanoids Pages: 787-788 !ifficulty: 2 "ns: B Which of the following is not true of the reaction %roducing &alonyl-CoA during fatty acid synthesis?

A) B) C) !) #)

't is sti&ulated (y citrate) 't requires acyl carrier %rotein (AC*)) 't requires CO (or (icar(onate)) One &ole of A+* is con,erted to A!* - *i for each &alonyl-CoA synthesi.ed) +he cofactor is (iotin)

$. Biosynthesis of fatty acids and eicosanoids Pages: 788-7 % !ifficulty: $ "ns: ! 'f &alonyl-CoA is synthesi.ed fro& /0CO and unla(eled acetyl-CoA1 and the la(eled &alonate is then used for fatty acid synthesis1 the final %roduct (fatty acid) will ha,e radioacti,e car(on in2

A) B) C) !) #)

e,ery C) e,ery e,en-nu&(ered C-ato&) e,ery odd-nu&(ered C-ato&) no %art of the &olecule) only the o&ega-car(on ato& (farthest car(on fro& C-/))

&. Biosynthesis of fatty acids and eicosanoids Page: 7 % !ifficulty: 2 "ns: # Which one of the following state&ents (est a%%lies to synthesis of fatty acids in E. coli e3tracts?

A) B) C) !)

Acyl inter&ediates are thioesters of a low &olecular weight %rotein called acyl carrier %rotein) CO or HCO3 is essential) 4educing equi,alents are %ro,ided (y $A!*H +he ulti&ate source of all the car(on ato&s in the fatty acid %roduct is acetyl-CoA)

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Chapter 21 Lipid Biosynthesis

#) All of the a(o,e are true)


'. Biosynthesis of fatty acids and eicosanoids Pages: 7 &-7 ' !ifficulty: 2 "ns: ! 'n co&%aring fatty acid (iosynthesis with o3idation of fatty acids1 which of the following state&ents is incorrect?

A) A thioester deri,ati,e of crotonic acid (trans- -(utenoic acid) is an inter&ediate in the synthetic B) C) !) #)
%ath1 (ut not in the degradati,e %ath) A thioester deri,ati,e of !--hydro3y(utyrate is an inter&ediate in the synthetic %ath1 not in the degradati,e %ath) 5atty acid (iosynthesis uses $A!*H e3clusi,ely1 whereas o3idation uses $A!- e3clusi,ely) 5atty acid degradation is cataly.ed (y cytosolic en.y&es6 fatty acid synthesis (y &itochondrial en.y&es) +he condensation of two &oles of acetyl-CoA in the %resence of a crude e3tract is &ore ra%id in (icar(onate (uffer than in %hos%hate (uffer at the sa&e %H6 the clea,age of acetoacetyl-CoA %roceeds equally well in either (uffer)

(. Biosynthesis of fatty acids and eicosanoids Page: 7 & !ifficulty: 2 "ns: ! #n.y&es that cataly.e the synthesis of long chain fatty acids in ,erte(rate cells2

A) B) C) !) #)

act as se,en se%arate %roteins) are encoded in &itochondrial genes) are locali.ed in the &itochondrial &atri3) are %art of a single %oly%e%tide chain containing se,eral distinct en.y&e acti,ities) ha,e none of the characteristics a(o,e)

7. Biosynthesis of fatty acids and eicosanoids Page: 7 ' !ifficulty: 2 "ns: # Which of the following is not true of the fatty acid synthase and the fatty acid -o3idation syste&s?

A) B) C) !) #)

A deri,ati,e of the ,ita&in %antothenic acid is in,ol,ed) Acyl-CoA deri,ati,es are inter&ediates) !ou(le (onds are o3idi.ed or reduced (y %yridine nucleotide coen.y&es) +he %rocesses occur in different cellular co&%art&ents) +he %rocesses occur in the &itochondrial &atri3)

8. Biosynthesis of fatty acids and eicosanoids Pages: 7 '-7 ( !ifficulty: 2 "ns: ! +he rate-li&iting ste% in fatty acid synthesis is2

A) B) C) !) #)

condensation of acetyl-CoA and &alonyl-CoA) for&ation of acetyl-CoA fro& acetate) for&ation of &alonyl-CoA fro& &alonate and coen.y&e A) the reaction cataly.ed (y acetyl-CoA car(o3ylase) the reduction of the acetoacetyl grou% to a -hydro3y(utyryl grou%)

Chapter 21 Lipid Biosynthesis

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. Biosynthesis of fatty acids and eicosanoids Page: 7 7 !ifficulty: 2 "ns: # Which of the following is not true of the fatty acid elongation syste& of ,erte(rate cells?

A) B) C) !) #)

't in,ol,es the sa&e four-ste% sequence seen in the fatty acid synthase co&%le3) 't is located in the s&ooth endo%las&ic reticulu&) 't %roduces stearoyl-CoA (y the e3tension of %al&itoyl-CoA) 't uses &alonyl-CoA as a su(strate) +he i&&ediate %recursor of the added car(ons is acetyl-CoA)

1%. Biosynthesis of fatty acids and eicosanoids Page: 7 7 !ifficulty: 2 "ns: " Which of these can (e synthesi.ed (y %lants (ut not (y hu&ans?

A) B) C) !) #)

7inoleate 8/92 (:1/ ); *al&itate (/<2=) *hos%hatidylcholine *yru,ate >tearate (/92=)

11. Biosynthesis of fatty acids and eicosanoids Page: 7 8 !ifficulty: $ "ns: B +he en.y&e syste& for adding dou(le (onds to saturated fatty acids requires all of the following except:

A) B) C) !) #)

a &i3ed-function o3idase) A+*) cytochro&e b?) &olecular o3ygen (O )) $A!*H)

12. Biosynthesis of fatty acids and eicosanoids Pages: 8%%-8%1 !ifficulty: $ "ns: " Which of these state&ents a(out eicosanoid synthesis is true?

A) B) C) !) #)

An early ste% in the %ath to thro&(o3anes is (loc@ed (y i(u%rofen) Arachidonate is deri,ed &ainly (y hydrolysis of triacylglycerols) As%irin acts (y (loc@ing the synthesis of arachidonate) *lants can synthesi.e leu@otrienes1 (ut hu&ans cannot) +hro&(o3anes are %roduced fro& arachidonate ,ia the AlinearB %ath)

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Chapter 21 Lipid Biosynthesis

1$. Biosynthesis of triacylglycerols Page: 8%& !ifficulty: 2 "ns: B +he (iosynthesis of triacylglycerols fro& acetate occurs &ainly in2

A) B) C) !) #)

ani&als (ut not in %lants) hu&ans after ingestion of e3cess car(ohydrate) hu&ans with low car(ohydrate inta@e) %lants (ut not in ani&als) none of the a(o,e)

1&. Biosynthesis of triacylglycerols Page: 8%' !ifficulty: 2 "ns: ! +he synthesis of (oth glycero%hos%holi%ids and triacylglycerols in,ol,es2

A) B) C) !) #)

C!*-choline) C!*-diacylglycerol) %hos%hatidate %hos%hatase) %hos%hatidic acid) %hos%hoethanola&ine)

1'. Biosynthesis of triacylglycerols Page: 8%( !ifficulty: 2 "ns: B Which of these state&ents a(out triacylglycerol synthesis is correct?

A) B) C) !) #)

Hu&ans can store &ore energy in glycogen than in triacylglycerols) 'nsulin sti&ulates con,ersion of dietary car(ohydrate into triacylglycerols) 't is not a hor&one-sensiti,e %rocess) "a&&als are una(le to con,ert car(ohydrates into triacylglycerols) *hos%hatidate is not on the %athway of triacylglycerol synthesis)

1(. Biosynthesis of )e)*rane phospholipids Pages: 8%8-81$ !ifficulty: 2 "ns: C A strategy that is not e&%loyed in the synthesis of %hos%holi%ids is2

A) B) C) !) #)

condensation of C!*-alcohol with diacylglycerol) condensation of C!*-diacylglycerol with alcohol) condensation of C!*-diacylglycerol with C!*-alcohol) e3change of free alcohol with head grou% alcohol of %hos%holi%id) re&odeling of head grou% alcohols (y che&ical &odification

17. Biosynthesis of )e)*rane phospholipids Pages: 81%-811 !ifficulty: 2 "ns: # All glycerol-containing %hos%holi%ids are synthesi.ed fro&2

A) cardioli%in B) cera&ide)

Chapter 21 Lipid Biosynthesis

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C) gangliosides) !) &e,alonate) #) %hos%hatidic acid)


18. Biosynthesis of )e)*rane phospholipids Page: 811 !ifficulty: 2 "ns: # 'n E. coli the synthesis of %hos%hatidylethanola&ine directly in,ol,es2

A) B) C) !) #)

acyl carrier %rotein) (iotin) C!*-choline) %hos%hatidylglycerol) serine)

1 . Biosynthesis of )e)*rane phospholipids Page: 812 !ifficulty: 2 "ns: ! 'n the synthesis of %hos%hatidylcholine fro& %hos%hatidylethanola&ine1 the &ethyl grou% donor is2

A) B) C) !) #)

a tetrahydrofolate deri,ati,e) choline) &ethanol) S-adenosyl&ethionine (ado"et)) serine)

2%. Biosynthesis of )e)*rane phospholipids Page: 81$ !ifficulty: 1 "ns: ! *al&itoyl-CoA1 1 is a direct %recursor of2

A) B) C) !) #)

cholesterol) &alonyl-CoA) &e,alonate s%hingosine) squalene)

21. Biosynthesis of )e)*rane phospholipids Page: 81$ !ifficulty: $ "ns: # C!*-diglyceride is not in,ol,ed in the (iosynthesis of2

A) B) C) !) #)

%hos%hatidylcholine) %hos%hatidylethanola&ine %hos%hatidylglycerol) %hos%hatidylserine) s%hingo&yelin)

22. Biosynthesis of )e)*rane phospholipids Page: 81' !ifficulty: 2 "ns: C Which of the following is true of s%hingoli%id synthesis?

A) All of the car(on ato&s of %al&itate and serine are incor%orated into s%hingosine)

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Chapter 21 Lipid Biosynthesis

C!*-s%hingosine is the acti,ated inter&ediate) CO is %roduced during the synthesis of cera&ide fro& %al&itate and serine) Clucose <-%hos%hate is the direct %recursor of the glucose in cere(rosides) *hos%hatidic acid is a @ey inter&ediate in the %athway) 2$. Biosynthesis of cholesterol+ steroids and isoprenoids Pages: 81(-81 !ifficulty: 2 "ns: B Which of the following is not an inter&ediate in the synthesis of lanosterol fro& acetyl-CoA?

B) C) !) #)

A) B) C) !) #)

'so%entenyl %yro%hos%hate "alonyl-CoA "e,alonate >qualene -Hydro3y- -&ethylglutaryl-CoA (H"C-CoA)

2&. Biosynthesis of cholesterol+ steroids and isoprenoids Page: 817 !ifficulty: 1 "ns: " Cholesterol is synthesi.ed fro&2

A) B) C) !) #)

acetyl-CoA) choline) li%oic acid) &alate) o3alate)

2'. Biosynthesis of cholesterol+ steroids and isoprenoids Pages: 818-81 !ifficulty: 1 "ns: # A 3=-car(on %recursor of the steroid nucleus is2

A) B) C) !) #)

farnesyl %yro%hos%hate) geranyl %yro%hos%hate) iso%entenyl %yro%hos%hate) lysolecithin) squalene)

2(. Biosynthesis of cholesterol+ steroids and isoprenoids Page: 818 !ifficulty: 2 "ns: C Which of these state&ents a(out cholesterol synthesis is true?

A) Cholesterol is the only @nown natural %roduct whose (iosynthesis in,ol,es iso%rene units) B) Only half of the car(on ato&s of cholesterol are deri,ed fro& acetate) C) >qualene synthesis fro& farnesyl %yro%hos%hate results in the release of two &oles of ** i for
each &ole of squalene for&ed)

!) +he acti,ated inter&ediates in the %athway are C!*-deri,ati,es) #) +he condensation of two fi,e-car(on units to yield geranyl %yro%hos%hate occurs in a Ahead-toheadB fashion)

Chapter 21 Lipid Biosynthesis

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27. Biosynthesis of cholesterol+ steroids and isoprenoids Page: 82% !ifficulty: 2 "ns: " Which of the following is deri,ed fro& a sterol? A) Bile salts B) Cangliosides C) Ceraniol !) *hos%hatidylglycerol #) *rostaglandins 28. Biosynthesis of cholesterol+ steroids and isoprenoids Pages: 82'-82( !ifficulty: 2 "ns: " Which of these state&ents a(out the regulation of cholesterol synthesis is not true? A) Cholesterol acquired in the diet has essentially no effect on the synthesis of cholesterol in the li,er) B) 5ailure to regulate cholesterol synthesis %redis%oses hu&ans to atherosclerosis) C) High intracellular cholesterol sti&ulates for&ation of cholesterol esters) !) 'nsulin sti&ulates H"C-CoA reductase) #) >o&e &eta(olite or deri,ati,e of cholesterol inhi(its H"C-CoA reductase) 2 . Biosynthesis of cholesterol+ steroids and isoprenoids Page: 828 !ifficulty: 2 "ns: ! Which of these co&%ounds is not synthesi.ed (y a %athway that includes iso%rene %recursors?

A) B) C) !) #)

$atural ru((er *lastoquinone Dita&in A Dita&in B/ Dita&in E

,hort "ns-er Questions


$%. Biosynthesis of fatty acids and eicosanoids Page: 78 !ifficulty: $ 'n the con,ersion shown (elow (which occurs during fatty acid synthesis)1 if the co&%ound on the left were la(eled with /0C in its &iddle car(on (F)1 where would the la(el (e in the co&%ound on the right? Circle the ato&s that would (e la(eled) ($ot all reactants are shown))

"ns: +he co&%ound on the right1 (utyryl-AC*1 would (e la(eled in C- (C-/ is the acyl car(on))

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Chapter 21 Lipid Biosynthesis

$1. Biosynthesis of fatty acids and eicosanoids Page: 78 !ifficulty: 2 +he reaction sequence that leads to fatty acid synthesis includes (/) condensation1 ( ) first reduction reaction1 (3) dehydration1 and (0) second reduction) >how the first reduction reaction1 with any required cofactors) "ns: -@etoacyl-AC* - $A!*H - H- hydro3yacyl-AC* - $A!*(>ee 5ig) /- 1 %) G9:)) $2. Biosynthesis of fatty acids and eicosanoids Pages: 7 %-7 1 !ifficulty: 2 5atty acid synthesis and fatty acid (rea@down occur (y si&ilar %athways) !escri(e1 ,ery (riefly1 four ways in which the synthetic and (rea@down %athways differ) "ns: 5atty acid synthesis (in any order) (/) e&%loys $A!*H as reducing agent6 ( ) in,ol,es an acyl grou% (ound to a %rotein1 AC*6 (3) ta@es %lace in the cytosol of ani&als6 (0) in,ol,es the condensation of &alonyl- and acetyl-grou%s6 (?) in,ol,es the for&ation of the !- -hydro3yacyl deri,ati,e) 5atty acid (rea@down (/) e&%loys $A!- as electron acce%tor6 ( ) in,ol,es acyl grou%s (ound to coen.y&e A6 (3) occurs in the &itochondrial &atri36 (0) does not in,ol,e &alonylderi,ati,es6 (?) in,ol,es the 7-stereoiso&er of the -hydro3yacyl deri,ati,e) $$. Biosynthesis of fatty acids and eicosanoids Pages: 7 %-7 1 !ifficulty: 2 +he synthesis of fatty acids and their (rea@down (y o3idation occur (y se%arate %athways) Co&%are the two %aths (y filling in the (lan@s (elow) (>o&e (lan@s &ay require &ore than one answer)) >ynthesis o3idation HHHHHHHHHHHHHHHHHH IIIIIIIIIIIIIII IIIIIIIIIIIIII IIIIIIIIIIIIIII IIIIIIIIIIIIII IIIIIIIIIIIIIII IIIIIIIIIIIIII IIIIIIIIIIIIIII IIIIIIIIIIIIII

Acti,ating grou% #lectron carrier coen.y&e(s) Basic units added or re&o,ed Cellular location of %rocess "ns:

>ynthesis o3idation HHHHHHHHHHHHHHHHHHHH Acti,ating grou% #lectron carrier coen.y&e(s) Basic units added or re&o,ed Cellular location of %rocess acyl carrier %rotein $A!*H &alonyl- and acetylcytosol in ani&als1 chloro%last in %lants CoAH>H $A!acetyl&itochondrial &atri3

$&. Biosynthesis of fatty acids and eicosanoids Page: 7 2 !ifficulty: $ >how the structure of each inter&ediate in the con,ersion of -hydro3y(utyryl-AC* to (utyryl-AC*

Chapter 21 Lipid Biosynthesis

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(y the fatty acid synthetase co&%le3) >how where cofactors %artici%ate) 'n your first inter&ediate1 circle the car(on ato&s that are deri,ed fro& &alonyl-CoA) "ns: -hydro3y(utyryl-AC* is first dehydrated1 yielding trans- -(utenoyl-AC*1 which is then reduced to (utyryl-AC*1 with $A!*H as the reducing agent) (>ee 5ig) /-?1 %) G: )) $'. Biosynthesis of fatty acids and eicosanoids Pages: 7 &-7 ( !ifficulty: $ !escri(e the &echanis& for &o,ing acetyl-CoA %roduced in the &itochondrial &atri3 into the cytosol for fatty acid synthesis) "ns: Acetyl-CoA in the &itochondrial &atri3 condenses with o3aloacetate to for& citrate in a reaction cataly.ed (y citrate synthase) Citrate &o,es out of the &atri3 ,ia the citrate trans%orter) Citrate in the cytosol is clea,ed (y citrate lyase1 yielding acetyl-CoA and o3aloacetate) +o co&%lete the cycle1 o3aloacetate in the cytosol is reduced to &alate1 which &o,es into the &itochondrial &atri3 on the &alate--@etoglutarate trans%orter1 and is con,erted to o3aloacetate in the &atri3) $(. Biosynthesis of fatty acids and eicosanoids Page: 8%% !ifficulty: 2 #3%lain (riefly why we require fats in our diets) "ns: !ietary fats %ro,ide the linoleate and linolenate that we need (for eicosanoid synthesis) (ut cannot synthesi.e) $7. Biosynthesis of fatty acids and eicosanoids Page: 8%1 !ifficulty: $ >@etch the %athway fro& arachidonate to thro&(o3anes and e3%lain how as%irin (loc@s the synthesis of thro&(o3anes) "ns: (>ee 5ig) /-/?1 %) 9=/)) $8. Biosynthesis of )e)*rane phospholipids Page: 8% !ifficulty: 2 !escri(e two (asic strategies for acti,ating %recursors in the (iosynthesis of %hos%holi%ids) "ns: (/) Acti,ate the head grou% (y attach&ent to C!*1 as in C!*-choline1 then dis%lace C"* with the hydro3yl grou% of glycerol in diacylglycerol) ( ) Acti,ate diacylglycerol (y the attach&ent of C!*1 then dis%lace C"* with the hydro3yl grou% of the head grou%) $ . Biosynthesis of )e)*rane phospholipids Pages: 81%-812 !ifficulty: 2 >how the (iosynthetic %ath(s) fro& %hos%hatidic acid to %hos%hatidylcholine) Jou &ay use shorthand notation for %hos%hatidic acid1 (ut na&e any cofactors required in the %ath and show where they are in,ol,ed) "ns: *hos%hatidic acid condenses with C+* to for& C!*-diacylglycerol6 then serine dis%laces C"*1 yielding %hos%hatidylserine) !ecar(o3ylation of %hos%hatidylserine yields %hos%hatidylethanola&ine1 and &ethylation of the a&ino grou% of %hos%hatidylethanola&ine with three &ethyl grou%s1 each donated (y S-adenosyl&ethionine1 yields %hos%hatidylcholine) (>ee 5igs)

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Chapter 21 Lipid Biosynthesis

/- ?1 %)9/=1 and 5ig) /- G1 %) 9/ )) 'n an alternati,e %ath1 %hos%hocholine condenses with C+*1 for&ing C!*-choline6 %hos%hatidic acid is de%hos%horylated to yield diacylglycerol6 and diacylglycerol dis%laces C"* fro& C!*-choline1 for&ing %hos%hatidylcholine) (>ee 5ig) /- <1 %) 9//)) &%. Biosynthesis of cholesterol+ steroids+ and isoprenoids Pages: 81( !ifficulty: 2 !escri(e (riefly the four stages in the %athway fro& acetyl-CoA to lanosterol) "ns: (/) synthesis of &e,alonate fro& acetate6 ( ) con,ersion of &e,alonate to two acti,ated iso%renes (iso%entenyl %yro%hos%hate and di&ethylallyl %yro%hos%hate)6 (3) condensation of si3 acti,ated iso%rene units to for& squalene6 (0) cycli.ation of squalene to for& the steroid nucleus of lanosterol) (>ee 5ig) /-331 %) 9/<)) &1. Biosynthesis of cholesterol+ steroids+ and isoprenoids Pages: 817 !ifficulty: 2 >how the reaction that li&its the rate of cholesterol synthesis fro& acetate1 indicating the role of any cofactors that %artici%ate) "ns: +his is the reaction cataly.ed (y H"C-CoA reductase) $A!*H is the cofactor) (>ee 5ig) /301 %) 9/G)) &2. Biosynthesis of cholesterol+ steroids+ and isoprenoids Page: 817 !ifficulty: $ >how the %athway fro& acetyl-CoA to &e,alonate1 indicating the roles of any cofactors) "ns: (>ee 5ig) /-301 %) 9/G)) &$. Biosynthesis of cholesterol+ steroids+ and isoprenoids Page: 817 !ifficulty: 2 >how the %athway fro& &e,alonate to di&ethylallyl %yro%hos%hate1 indicating where any cofactors %artici%ate) "ns: (>ee 5ig) /-3?1 %) 9/G)) &&. Biosynthesis of cholesterol+ steroids+ and isoprenoids Page: 817 !ifficulty: $ +he synthesis of cholesterol (egins with the condensation of a four-car(on unit fro& IIIIIIIIIIIIIII with the two car(ons of acetyl-CoA to for& a si3-car(on deri,ati,e) Ci,e its structure1 and circle the ato&s that originated in the acetyl-CoA) "ns: Acetoacetyl-CoA6 +he si3-car(on %roduct is -hydro3y- -&ethylglutaryl-CoA (H"C-CoA)) (+he structure and car(ons originating in acetyl-CoA are shown in 5ig) /-301 %) 9/G)) &'. Biosynthesis of cholesterol+ steroids+ and isoprenoids Page: 818 !ifficulty: 2 !escri(e the for&ation of farnesyl %yro%hos%hate fro& acti,ated iso%renyl units) "ns: +his is the reaction in which di&ethylallyl %yro%hos%hate condenses head-to-tail with iso%entenyl %yro%hos%hate1 with the eli&ination of **i) (>ee 5ig) /-3<1 %) 9/9))