AminoAcidsandproteins

M1lecture
Marie-Vronique CLEMENT AssociateProfessor YongLooLinSchoolofMedicine NUSGraduateSchoolforIntegrativeScienceandEngineering DepartmentofBiochemistry NationalUniversityofSingapore 8MedicalDrive,MD7#0315 Singapore117597 Tel:(65)68747985 Fax:(65)67791453 Email: bchmvc@nus.edu.sg

Didyouknow?

Aminoacidsareamongthemost commonnutritionalsupplements takenbyathletes

Effectofproteinandaminoacidsupplementationonathleticperformance, RichardBkreider,phD

Why?

Aminoacidsaremajorconstituentforbrain, nerve,muscle,blood,skinandinternalorgans.

yourbody,minuswater,is: 75percentaminoacids 95percentofhormonesareaminoacids 100percentofallproteinisaminoacids

Beware!!

3differentwaystoidentifyaminoacids

20aminoacids:

9Essentialaminoacids
cannotbemanufacturedbythebody

11Nonessentialaminoacids(+selenocystein)
canbemanufacturedbythebodywithpropernutrition.

Alanine Arginine AsparticAcid Asparagine CysteineCystine

GlutamicAcid Lysine Glutamine Glycine Histidine Isoleucine Leucine Methionine

Threonine Tryptophan

Phenylalanine Tyrosine Proline Serine Valine

Howtoremembertheessentialaminoacid?
cannotbemanufactured bythebody

Ahelpfulmnemonicfor rememberingessentialamino acidsis

"PrivateTimHall (PVTTIMHALL)
P V T T I M H A L L

Alanine Notrequiredinadult Butrequiredininfantdiet

Whereareaminoacidscomingfrom?

Fromthevarietyoffoodsinourdiet
Meat,milk,cheese,andeggarecompleteproteinsthathavealltheessential aminoacids. Othersourcesofproteinincludewholegrains,rice,corn,beans,legumes, oatmeal,peas,andpeanutbutter. Forvegetarians,vegansand/orthosewhodonoteatmeat,fish,eggs,or dairyproducts,itisimportanttoeatavarietyoftheseotherfoodsinorderto getenoughprotein.

Essentialaminoacids
comefrombreakdown ofproteinsfromourfood

Nonessential aminoacid
aremetabolizedinourbody fromglucose

Glycolysisandthecitricacidcycle providetheprecursorsneededtosynthesizemanyimportant biologicalmoleculesincludingaminoacids

/Chapter2

Thegeneralformulaofanaminoacid:
acarbonatom

Amino group

Carboxylgroup

Sidechain

Fewexamplesofspecificsidechains

Thesimplest aminoacid

Themost occurentinprotein (9.2%)

Theleast occurentinprotein (1.4%) Side chains

Readchapter3/ Devlinp9598for moredetails

2 Enantiomers

Byconvention,ifNH3+isprojectedtotheleft, theaminoacidhasanLconfiguration.

Notanaminoacid
Itisthesimplestofallcommon aldoses.Itisasweetcolorless crystallinesolidthatisan intermediatecompoundin carbohydratemetabolism

Inmammalianproteinsonlyaminoacidof Lconfigurationarefound.

LAlanine(Ala/A)

LAsparagine(Asn/N) LArginine(Arg/R)

LAsparticacid(Asp/D)

LThreonine(Thr/T)

OR
Unsubstituted Heterocyclic Aromatic Thioether hydroxy Mercapto Carboxiamide Monoamino, dicarboxylic Diamino,monocarboxylic NonPolar Polarcharged Polaruncharged

Polar/nonPolar:thedefinition
Polarmolecules
Polarmoleculesaregenerallyabletodissolveinwater(hydrophilic)duetothe polarnatureofwater.Polarmoleculeshaveslightlypositiveandslightlynegatively chargedends. Examplesofhouseholdpolarmoleculesincludetablesalt,ammoniaandsugar (glucose).

Nonpolarmolecules
Mostnonpolarmoleculesarewaterinsoluble(hydrophobic)atroomtemperature. Examplesofhouseholdnonpolarcompoundsincludefats,oilandpetrol.

Polar: Nonpolar:

hydrophilic hydrophobic

hyrophobic

Hydrophylic

?
Hydrophylic

AminoacidareinanionizedformatpH7

AtpH7:
Amino Group
(protonatedinits amoniun anionform)

Carboxylicacid Group
(unprotonatedinits carboxylateionform

Hydrogen atom

IonizationStateasaFunctionofpH.Theionization stateofaminoacidsisalteredbyachangeinpH.The zwitterionicformpredominatesnearphysiologicalpH.

Glycine

Histidine

Ionizable sidechain

3acid/basegroups

Leucine 2acid/basesites

Glutamic acid 3acid/base sites

AminoAcids Buildingblockofproteins 9essential 11nonessential

20AminoAcids:

Generalformula ofanAminoAcid
Unsubstituted Heterocyclic Aromatic Thioether hydroxy Mercapto Carboxiamide Monoamino, dicarboxylic Diamino,monocarboxylic

Allaminoacidshaveaspecificsidechain

AllaminoacidsareintheLconfiguration Aminoacidsidechaincanbe polar/hydrophilic Nonpolar/hydrophobic

Aminoacids viewtroughphotomicrographs(photographstakenthroughamicroscope)

Arginine

Valine

Alanine
micro.magnet.fsu.edu/micro/gallery/aminoacid/aminoacid.html

Lysine

acid

base

Thetitrationcurveofaceticacid (CH3COOH). ThepKaforthedissociationofaceticacid tohydrogenandacetateionsis4.75. AtthispH,halftheacidmoleculesare dissociated. BecausepHismeasuredonalogarithmic scale,thesolutionchangesfrom91 percentCH3COOHatpH3.75to9 percentCH3COOHatpH5.75. Theacidhasmaximumbufferingcapacity inthispHrange.

pH = pKa when [A-] = [HA] [HA]

Thefourmainfamiliesofsmallorganicmolecules incells

Aminoacidsareweakacidsbecauseoftheirionizablegroups