BiologicallyImportantCompounds

Carbohydrates
1WhichofthefollowingisaDaldopentose?

2.WhichofthefollowingisanLsaccharide?

3(+)Arabinoseis(2R,3S,4S)aldopentose.Whichofthefollowingis(+)arabinose?

4Whichofthefollowinggivesanopticallyinactivealdaricacidonoxidationwithdilutenitricacid?

5Whichtwoofthefollowingcompoundsarereducedtothesamechiralalditolbysodiumborohydride?

A)1&2
B)2&3
C)3&4
D)2&3
6Whichofthefollowingstatementsiscorrect?
A)TheRuffprocedurelengthensanaldosechainandgivesasingleproduct.
B)TheRuffprocedureshortensanaldosechainandgivestwoepimers.
C)TheKilianiFischerprocedureshortensanaldosechainandgivesasingleproduct.
D)TheKilianiFischerprocedurelengthensanaldosechainandgivestwoepimers.
7Whichtwoofthefollowingcompounds,ifany,areepimers?

A)1&4
B)1&3
C)2&3
D)3&4
8Whichofthefollowingisnotadisaccharide?
A)sucrose
B)mannose
C)lactose
D)maltose
9Whichofthefollowingisnotareducingsugar?
A)sucrose
B)mannose
C)lactose
D)fructose
10Whichtwoofthefollowingaldohexosesgivethesameosazonederivative?

A)1&4

B)1&3
C)2&3
D)3&4
11Whichstatementaboutthepyranoseformofmannoseisnotcorrect?
A)itexistsastwoanomericstereoisomers.
B)itreactswithTollens'reagenttogiveasilvermirror.(i.e.itisareducingsugars)
C)reactionwithexcessCH3IandAgOHgivesanonreducingpentaOmethylderivative.
D)itresistsreductionwithaqueoussodiumborohydride.
12TwoaldopentosesXandYgivethesameosazonederivative.
Xisoxidizedtoanopticallyactivealdaricacidbydilutenitricacid.
RuffdegradationofYgaveatetrosewhichwassimilarlyoxidizedtoanopticallyactivealdaricacid
AssignthestructuresofXandYfromthefollowinglist?

A)X=1&Y=4
B)X=4&Y=1
C)X=2&Y=3
D)X=3&Y=2
13Whichofthestructures1through4ismethylDgalactopyranoside?

A1

B2

C3

D4

14Whatisinvertsugar,andwhyisitsonamed?
A)thesugarmixturefromhydrolysisofsucrosefructoseisisomerizedtoglucose.
B)thesugarmixturefromhydrolysisofsucrosetheopticalrotationchangesfrom(+)to().
C)thesugarmixturefromhydrolysisofstarchglycosidicbondsarechangedtoglycosidicbonds.
D)thesugarmixturefromhydrolysisofstarchglucoseisisomerizedtofructose.

15Whichofthefollowingcompoundsisaaldopentafuranose?

A1

B2

C3

D4

16Whichofthefollowingcompoundsisaketohexafuranose?

A1

B2

C3

D4

17Whichofthefollowingdisaccharidesistheanomerof4O(Dglucopyranosyl)Dglucopyranose?

A1

B2

C3

D4

18Whichofthefollowingdisaccharidesisanonreducingsugar(doesnotreactwithTollens'reagent)?

A1

B2

C3

D4

19Whichofthefollowingbestdescribesthepolysaccharideamylose?
A)a1,4OlinkedpolyDglucose
B)a1,4OlinkedpolyDglucose
C)analternating1,4O/linkedpolyDglucose
D)a1,4OlinkedpolyDmannose
20Whichofthefollowingdisaccharidesistheanomerof4O(Dglucopyranosyl)Dglucopyranose?

A1

B2

C3

D4

21Whichofthefollowingbestdescribesthepolysaccharidecellulose?
A)a1,4OlinkedpolyDgalactose
B)a1,4OlinkedpolyDgalactose
C)a1,4OlinkedpolyDglucose
D)a1,4OlinkedpolyDglucose
22WhenoctaOmethylDcellobioseishydrolyzedbyaqueousacid,twoOmethyatedglucosederivativesare
formed.
Oneisatetramethylderivative,andtheotherisatrimethylderivative.
Whyisasinglemethylsubstituentlostinthisprocess?
A)onemethoxygroupislostbyelimination.
B)onemethoxygroupisanesterandtheothersareallethers.

C)onemethoxygroupispartofanacetal,theothersareallethers.
D)oneglucoseisanmethylglycosidetheotherisamethylglycoside.
23Gentiobiose(C12H22O11)isareducingsugar.Itformsanosazonederivativeandmutarotates.
HydrolysisofgentiobiosebytheenzymeemulsinproducesDglucoseastheonlyproduct.
Anoctamethylderivativeofgentiobioseishydrolyzedtoamixtureof2,3,4,6tetraOmethylglucoseand
2,3,4triOmethylglucose.
Whatisthestructureofgentiobiose(eitheranomer)?

A1

B2

C3

D4

24Trehalose(C12H22O11)isanonreducingsugar.HydrolysisbytheenzymemaltaseproducesDglucoseas
theonlyproduct.
Anoctamethylderivativeoftrehaloseishydrolyzedto2,3,4,6tetraOmethylglucoseastheonlyproduct.
Whatisthestructureoftrehalose?

A1

B2

C3

D4

25AcidcatalyzedreactionofDglucosewithbenzaldehydeproducesthe4,6Obenzylidenederivative.
ReductionwithNaBH4,followedbyexcessHIO4cleavageandacidhydrolysisyieldsaC4H8O4tetroseand
benzaldehyde.
Whatistheconfigurationofthistetrose?
A)2S,3S
B)2R,3S
C)2R,3R

D)2S,3R
26ADaldohexosegivesanopticallyinactivealdaricacidonoxidationwithnitricacid.
RuffdegradationofthisaldohexoseproducesanaldopentosethatisreducedbyNaBH4toanopticallyactive
alditol.
Whichofthefollowingisthishexose?

A1

B2

C3

D4

27MycaroseisarareC7H14O4sugarfoundinsomeantibioticnaturalproducts.
MycarosegivesapositiveTollens'test,doesnotformanosazonederivative,andonexhaustiveHIO4
oxidationgivesHCO2H,CH3CHOandCH3COCH2CHO.
Whichofthefollowingstructuresmightbemycarose?

A1

B2

C3

D4

28Iftwoisomershavebeenclassifiedcorrectlyasanomers,theymayalsobecalled...?
A)conformers
B)enantiomers
C)tautomers
D)diastereomers
AminoacidsandProteins
29BothcysteineandmethioninearechiralLaminoacidsthatincorporateasinglesulfur.TheC2
configurationisSinmethionine,butRincysteine.Why?

A)biosynthesisofcysteineproceedsbyinversionatC2.
B)thesulfurincysteinepreventszwitterionformation.
C)thesulfuratominmethionineisremotefromC2anddoesnotinfluencethesequencerule.
D)thesulfuratomincysteineisremotefromC2anddoesnotinfluencethesequencerule.
30Threonineis(2S,3R)2amino3hydroxybutanoicacid.
Whichofthefollowingisthreonine?

31WhichofthefollowingisthemajorsolutespeciesinasolutionofalanineatpH=2?

32WhichofthefollowingisthemajorsolutespeciesinasolutionofalanineatpH=6?

33WhichofthefollowingisthemajorsolutespeciesinasolutionoflysineatpH=10.8?

34WhichofthefollowingisthemajorsolutespeciesinasolutionofglutamicacidatpH=4.0?

35Ninhydrinreagentreactswithaminoacidstogiveapurplecolor.
Inthethereactionofninhydrinwithphenylalanine,whichofthefollowingisresponsibleforthiscolor?

A1

B2

C3

D4

36Whichofthefollowingstatementsmostcorrectlydefinestheisoelectricpoint?
A)thepHatwhichallmolecularspeciesareionizedandthatcarrythesamecharge.
B)thepHatwhichallmolecularspeciesareneutralanduncharged.
C)thepHatwhichhalfthemolecularspeciesareionized(charged)andtheotherhalfunionized.
D)thepHatwhichnegativelyandpositivelychargedmolecularspeciesarepresentinequal
concentration.
37AtripeptideiscomposedequallyofLvaline,LtyrosineandLalanine(onemoleculeofeach).
Howmanyisomerictripeptidesofthiskindmayexist?
A)three
B)four
C)six
D)eight
38Peptidesarecomposedofaminoacidsjoinedbyamidebonds.
Whichofthefollowingstatementsisnotcorrect?
A)amidegroupsaremoreresistanttohydrolysisthanaresimilarestergroups.
B)presonancestabilizestheamidebond.
C)stableconformationsofpeptidesarerestrictedtothosehavingplanaramidegroups.
D)amidegroupsdonotparticipateinhydrogenbondinginteractions.
39TheStreckersynthesisofaminoacidsbeginswiththereactionofanaldehydewithammoniumchloride
andpotassiumcyanide.
Thisisfollowedbyanacidcatalyzedhydrolysis,thatgivestheaminoacid.
Whatfunctionalgroupishydrolyzedinthesecondstep?
A)anester
B)annitrile
C)anamide
D)animinederivative
40Themethylandethylestersofmanyaminoacidsaresoldcommerciallyastheirhydrochloridesalts.

Whyarethesederivativesnotsoldintheformoftheneutralaminoesters?
A)thesaltsaresolids,whereasmanyaminoestersareliquidsandaredifficulttopackage.
B)rearrangementtotheNalkylaminoacidtakesplace.
C)polymerizationtakesplacebyacylationofaminegroupsbyanester.
D)anextrastepintheirpreparationwouldberequired.
41Youhaveamixtureofthreeaminoacids:E(pI=3.2),Y(pI=5.7)&K(pI=9.7)
UnderelectrophoresisatpH=7.7,inwhichdirectionwilleachcomponentofthemixturemove?
A)EtoanodeY&Ktocathode
B)EtoanodeYstationaryKtocathode
C)EtocathodeYstationaryKtoanode
D)E&YtoanodeKtocathode
42Sanger'sreagent,2,4dinitrofluorobenzene,reactswithwhichfunctionalgroupsinapeptide?
A)freeaminogroups
B)thephenolichydroxylgroupintyrosine
C)thearomaticheterocyclicringsofhistidineandtryptophan
D)thesulfidegroupofmethionine
43Allthecommonaminoacids,saveone,reactwithcoldnitrousacid(HNO2)andevolvenitrogengas.
Whichofthefollowingaminoacidsisthatcompound?
A)cysteine
B)proline
C)histidine
D)arginine
44Theaminoacidcysteineoftenformsadisulfidebondwithanothernearbycysteine.
Howisthisreactionbestclassified?
A)anaddition
B)asubstitution
C)anoxidation
D)areduction
45AhexapeptidehasthecompositionAla,Gly,Phe,Val3.BoththeNterminalandCterminalunitsareVal.
Cleavageofthehexapeptidebychymotrypsingivestwodifferenttripeptides,bothhavingValastheN
terminalgroup.
AmongtheproductsofrandomhydrolysisisaAlaValdipeptidefragment.Whatistheprimarystructureof
thehexapeptide?
A)ValGlyPheValAlaVal
B)ValAlaPheValGlyVal
C)ValGlyAlaValPheVal
D)ValPheValAlaGlyVal
46AnoctapeptidehasthecompositionAla 2,Gly2,Phe 2,Ser2.TheNterminalunitisAla.

Cleavageoftheoctapeptidebychymotrypsingivesasingletetrapeptide,havingAlaasitsNterminalgroup.
AmongtheproductsofrandomhydrolysisisaPheAlaGlytripeptidefragment.Whatistheprimary
structureoftheoctapeptide?
A)AlaGlySerPhePheSerGlyAla
B)AlaSerGlyPheAlaGlySerPhe
C)AlaSerGlyPheAlaSerGlyPhe
D)AlaGlySerPheAlaGlySerPhe
47Peptidebondformationfromprotectedaminoacidreactantsisoftencarriedoutwithwhichreagent?
A)ptoluenesulfonylchloride
B)ditbutyldicarbonate
C)dicyclohexylcarbodiimide
D)benzylchloroformate
48WhatreagentisusedintheEdmandegradationforNterminalgroupanalysisofpeptides?
A)phenylisothiocyanate
B)ditbutyldicarbonate
C)dicyclohexylcarbodiimide
D)benzylchloroformate
49Whichofthefollowingmethodsselectivelycleavesapeptideatmethionineresidues?
A)trypsindigestion.
B)cyanogenbromide.
C)chymotrypsindigestion.
D)Edmandegradation.
50Whichofthefollowingisnotanimportantsecondarystructuralfeatureinlargepeptidesandproteins?
A)thehelix.
B)theturn.
C)chairconformations.
D)thepleatedsheet.
51WhichofthefollowingstatementsistrueforphenylalanineinanaqueoussolutionatpH=pI?
A)thenonpolar,neutralspeciesC6H5CH2CH(NH2)CO2Histhemostabundantsolute.
B)theconcentrationsof[+]and[]chargedmolecularionsareequal.
C)racemizationisrapid.
D)thisconditionisimpossible,sincepHcanneverequalpI.
52Whichofthefollowingfactorshastheleastinfluenceonthesecondaryandtertiarystructuresof
proteins?
A)theachiralnatureofglycineunits.
B)sterichindranceofbulkysidechainsonthepeptidebackbone.
C)hydrogenbondingofC=OtoNHgroupslocatedneareachotherinspace.
D)conformationalrestrictionimposedbyprolineunits.

53Fromthereagentsinthefollowingtable,selecttheonebestusedtocleavepeptidechainsatArgandLys
residues.
1
ninhydrin

2
3
cyanogenbromide trypsin

4
chymotrypsin

5
phenylisothiocyanate

A5

B4

C3

D2

54Fromthereagentsinthefollowingtable,selecttheoneusedinacolortestforaminoacids.
1
ninhydrin

2
3
cyanogenbromide trypsin

4
chymotrypsin

5
phenylisothiocyanate

A1

B2

C3

D4

Lipids
55Fattyacidsareimportantcomponentsofmanylipids.Forwhichofthefollowinglipidclassesorlipid
derivativesarefattyacidsnotasignificantcomponent?
A)phospholipids
B)triglycerides
C)waxes
D)steroids
56Whichofthefollowingisageneralcharacteristicofthosenaturalproductsclassifiedaslipids?
A)theyaregenerallyinsolubleinwaterandsolubleinorganicsolvents.
B)theyaregenerallysolubleinwaterandinsolubleinorganicsolvents.
C)theyhavethecommonstructuralfeatureoftwoormorefusedcarbonrings.
D)theygenerallyhaveahighweightproportionofoxygen(>40%).
57Whichofthefollowingwouldbeclassifiedasasesquiterpene?

58Whichifanyofthefollowingisatriglyceride?

59Whichofthefollowingstatementsaboutglyceryltripalmitate,1,2,3propanetrioltris(hexadecanoate),is
nottrue?
A)itisreducedto1hexadecanolbylithiumaluminumhydride
B)itisachiral
C)ithasahighermeltingpointthanglyceryltrioleate
D)itaddsbromine
60Countingbothconstitutionalandstereoisomers,howmanyisomerictriglyceridesincorporatingoneoleic
acidandtwostearicacidgroupsexist?
A)one(therearenoisomers)
B)two
C)three
D)four
61Whichstatementcomparingthesoap.sodiumstearate,andthedetergentsodiumlaurylsulfateisnottrue?
A)bothformmicellesinwaterdispersion.
B)atpHbelow6.5thesoapprecipitates,thedetergentdoesnot.
C)thesoapislessalkaline(basic)thanthedetergent.
D)calciumsaltsofthesoaparerelativelyinsoluble.
62Whichofthefollowingwouldbeclassifiedasaprostaglandin?

63WhichofthefollowingisvitaminA?

64Spermaceti,C32H64O2,isasubstancefoundintheheadofthespermwhale.Itdisplaysastronginfrared
absorptionat1735cm1
LiAlH4reductionofspermacetigivesasingleC16H34Oalcohol
Whatclassoflipidsdoesspermacetibelong?
A)triglycerides
B)waxes
C)terpenes
D)transfattyacids
65Cembrene,aC20H32hydrocarbon,hasaUVmax=240nm.
Exhaustiveadditionofhydrogen(Pdcatalyst)gives4isopropyl1,7,11trimethylcyclotetradecane.
OzonolysisofcembrenewithaZndustworkupyieldseqimolaramountsofCH3COCH2CH2CHO,
CH3COCHO,
CH3COCH2CH2CH[CH(CH3)3]CHO&CH2(CHO)2
Whichofthefollowingisaplausiblestructureforcembrene(doublebondconfigurationsarenotspecified)?

NucleicAcids
66WhichofthefollowingisnotacommoncomponentofbothDNAandRNA?
A)ribose
B)phosphate
C)cytosine
D)adenine
67WhichofthefollowingisnotacomponentofRNA?
A)adenine

B)phosphate
C)cytosine
D)thymine
68Whichofthefollowingispurinebase?
A)guanine
B)indole
C)cytosine
D)thymine
69Whichofthefollowingisapyrimidinebase?
A)imidazole
B)guanine
C)cytosine
D)adenine
70TheHbondedbasepairshownontherightrepresentswhichofthefollowing?
A)adeninethymine
B)guaninecytosine
C)adeninecytosine
D)adenineguanine

71Whichofthefollowingisanucleoside?

72InDNAreplicationthecomplementarynucleotidesequencefor5'ACGT3'iswhichofthefollowing?
A)3'ACGT5'
B)3'TGCA5'
C)5'AGCT3'
D)5'TCGA3'
73WhatisthecomplementaryRNAsequencefortheDNAsegmentAATCAGTT?
A)AAUCAGUU
B)CCAUCGAA
C)AACUGAUU

D)UUAGUCAA
74Howmanynucleotidesareneededtocodeforaspecificaminoacid?
A)one
B)two
C)three
D)four
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