AminoAcids

AllmetabolicactivitiesoflivingbodiesareregulatedbyBiomolecules.TherearemainlyfourtypesofBiomolecules
whichtakepartinalmostallthemetabolicactivitiesoflivingcells.TheseBiomoleculesarecarbohydrates,lipids,
proteinsandnucleicacid.Thesearepolymericformsofsomemonomerunits.Forexampleproteinsarecomposed
ofaminoacidsthatarebondedwitheachotherthroughpeptidelinkage.
Aminoacidsareorganicmoleculeswithtwofunctionalgroupswhicharebondedtothesamecarbonatomofthe
molecule.Oneisanaminogroup(NH2)andanotheriscarboxylicgroup(COOH).Thecarbonatom,atwhichboth
ofthefunctionalgroupsarebonded,isknownasthealphacarbonatomandsuchaminoacidsareknownasalpha
aminoacids.Onlyalphaaminoacidsinvolveinthepolymerisationtoformproteinmolecule.Betaandgammaamino
acidscannotformproteinmolecules.
Theaminogroupofoneaminoacidisinvolvedinacondensationreactionwithcarboxylgroupofanotheraminoacid
toformCONHlinkage.Thislinkageiscalledasapeptidebond.Doyouknowboththefunctionalgroupsofan
aminoacidmoleculehavedifferentnature?Oneisacidicandanotherisalkalineinnature.Thenwhatwillbethe
natureofanaminoacidmolecule?Letsdiscussthepropertiesofdifferentaminoacidmolecules.

AminoAcidDefinition
Aminoacidsaregenerallyreferredas

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aminoacids.ThegeneralformulaforaminoacidisH2NCHRCOOH.

Here'R'isthefunctionalgroupoftheaminoacids.

Ballandstickmodel

Theaminogroupisattachedtothecarbonatomimmediatelynexttothecarboxylategroupthatis

carbon,so,it

aminoacids.Otheraminoacidsalsoexistcalledbetaandgammaaminoacids,inwhichtheamino
groupisattachedtothecarbonwhichisnextto carboncalled aminoacidandthenextiscalled amino
iscalled
acid.

ClassificationofAminoAcids

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Aminoacidsareclassifiedintodifferentwaysbasedonpolarity,structure,nutritionalrequirement,metabolic
fate, etc. Generally used classification is based on polarity. Amino acid polarity chart shows the polarity of amino
acids.
Basedonpolarity,aminoacidsareclassifiedintofourgroupsasfollows,
1. Nonpolaraminoacids
2. Polaraminoacidswithnocharge
3. Polaraminoacidswithpositivecharge
4. Polaraminoacidswithnegativecharge

Classificationbasedonpolarity
Amino acid are classified based on those with nonpolar R group, uncharged polar R group, charged polar R group.
Thenonpolarsidechainaminoacidsarecalledhydrophobicandtheaminoacidwithunchargedpolarsidechainis
called hydrophilic .Italsocontaintheacidsidechainsandbasicsidechains.

NonPolarAminoAcids
Non Polar Amino Acids have equal number of amino and carboxyl groups and are neutral. These amino acids are
hydrophobic and have no charge on the 'R' group. The amino acids in this group are alanine, valine, leucine,
isoleucine,phenylalanine,glycine,tryptophan,methionineandproline.

PolarAminoAcidswithPositiveCharge
Polar amino acids with positive charge have more amino groups as compared to carboxyl groups making it basic.
The amino acids which have positive charge on the 'R' group are placed in this category. They are lysine, arginine
andhistidine.

PolarAminoAcidswithnoCharge
Theseaminoacidsdonothaveanychargeonthe'R'group.Theseaminoacidsparticipateinhydrogenbondingof
proteinstructure.Theaminoacidsinthisgroupareserine,threonine,tyrosine,cysteine,glutamineandaspargine.

PolarAminoAcidswithNegativeCharge
Polar amino acids with negative charge have more carboxyl groups than amino groups making them acidic. The
amino acids which have negative charge on the 'R' group are placed in this category. They are called
as dicarboxylicmonoaminoacids .Theyareasparticacidandglutamicacid.

Classification based on the availability of amino acids. The amino acids which cannot be synthesized in the body
must be supplied to the body through diet are called essential amino acids. The amino acids which can be
synthesizedinthebodyarecalled nonessentialaminoacids.

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FunctionsofAminoAcid

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Aminoacidscanbefoundinmostofthenutrientsweeat.Aminoacidsarethebuildingblocksofhealthyprotein.If
thefoodconsumedisrichinprotein,ourbodydigeststheproteinrightdowntoindividualaminoacidsandlittlelinks
ofaminoacidsisadequatetobetakenoverintothebloodstream.
Themainpurposesofamino acids are to construct and rectify muscular tissue, but the uses go further than that.
Thesethingsdevelopchemicalssubstancethatgrantourmindstofunctionatitseminentpotential.

StructureofAminoAcid

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Aminoacidsarethebuildingblocksofproteins.Eachaminoacidcontains:
1. Aminogroup(NH2group
2. Carboxylgroup(COOHgroup)
3. Rgroup(sidechain)whichdeterminesthetypeofanaminoacid

All three groups are attached to a single carbon atom called chiral carbon. There are 20 common
aminoacidscharacterisedbydifferentRgroups.These20aminoacidscanbeclassifiedaccording
totheirmass,volume,acidity,polarityandhydrophobicity.

EssentialAminoAcids

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Outofthe20aminoacidsinproteins,humansareabletosynthesizeonly11,callednonessentialamino
acids,theother9calledessentialaminoacids,mustbeobtainedindiet.Thedivisionbetweenessentialand
nonessentialaminoacidsisnotclearcuthoweverTryosineforinstanceissometimesconsiderednonessential
becausehumanscanproduceitfromphenylalanine,butphenylalanineitselfisessentialandmustbeobtainedinthe
diet.Argininecanbesynthesizedbyhumans,butmuchofthearginineinproteinsalsocomesfromthediet.
Essentialaminoacidsarenotproducedbythebody.Wecangetthembyeatingcompleteproteinfoodsorfroma
combination of incomplete vegetables. The nine essential amino acids include histidine, isoleucine, leucine, lysine,
methionine, phenylalanine, tryptophan, and valine. The thirteen nonessential amino acids are alanine, arginine,
asparticacid,cysteine,cystine,glutamicacid,glutamine,glycine,hydroxyproline,proline,serine,andtyrosine.

Essentialaminoacids Nonessentialaminoacids
Histidine
Alanine
Isoleucine
Arginine
Leucine
Asparagine
Lysine
Asparticacid
Methionine
Cysteine
Phenylalanine
Glutamicacid
Threonine
Glutamine
Tryptophan
Glycine
Valine
Proline
Serine
Tyrosine

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StandardAminoAcids

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Thestandard20aminoacidsdiffer only in the structure of the side chain or R group. They can be subdivided into
smallergroupingsonthebasisofsimilaritiesinthepropertiesoftheirsidechains.
In addition to the 20 common amino acids there are nonstandard amino acids. Two nonstandard amino acids
whichappearinproteinsandcanbespecifiedbygeneticcodeareselenocysteine and pyrrolysine. There are also
nonstandardaminoacidswhichdonotappearinproteins.
Examplesincludelanthionine,2aminoisobutyricacidanddehydroalanine.Theyoftenoccurasintermediatesin
themetabolicpathwaysforstandardaminoacids.Somenonstandardaminoacidsareformedthroughmodification
to the Rgroups of standard amino acids. One example is hydroxyproline which is made by a post translational
modificationofproline.

PropertiesofAminoAcids

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Thegeneralpropertiesofaminoacidsarelistedbelow:
Solubility: Aminoacidsaresolubleinwater,acids,alkalies,butsparinglysolubleinorganicsolvents.
Color: Aminoacidsarecolorless,whitesolids.
State: Aminoacidsaresolidcrystallinecompounds.
Meltingpoints: Aminoacidshavehighmeltingpoints.
Duetopresenceofbasicandacidicgroupsinthesamemolecule,theymayberegardedassaltsandhence,
mostofthemeitherpossesshighermeltingpointormeltwithdecomposition.
Presenceofasymmetriccarbon

ExceptGlycine(thefirstmemberofaminoacidseries),alltheaminoacidscontainatleastoneasymmetric
carbonatomandhence,theyareopticallyactiveandcanexistindandlforms.
Butitisveryimportanttonotethatinnaturetheyneverexistintheracemicform.
Innaturetheyalwaysoccurintheopticallyactiveform.
AllthenaturallyoccurringaminoacidsarehavingLconfiguration.
AndthisLseriesofaminoacidsarebiologicallyactivecompounds.
They exist in the form of internal salt, zwitter ion. (as we know aminoacids have acidic and basic functional
groupsinit)
Aminoacidsandcarboxylicgroups

Decarboxylationofaminoacids

Deaminationofaminoacids

Ammoniumsaltsfromaminoacids

Carboxylatesaltsfromaminoacids

Zwitterions

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Sinceinaminoacidsbothcarboxylicgroup(COOH)andaminogroup(NH3)exists,inaqueoussolutiontheH+ion is
transformedfromoneendofthemoleculetotheotherendtoform zwitterions. Itisconsideredasbothelectrically
charged and electrically neutral also. Since it is having both the charges (positive and negative) the net charge of
zwitterioniszero.

Aminoacidinzwitterionformreactswithbothacidsandbasesanditshowstheamphotericbehavior.Thepointat
which the zwitter ion has no net charge is called Isoelectric point. At this point the amino acid is considered as
electricallyneutral.

IsoelectricPoint

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AnimportantpHvaluerelativetothevariousformsanaminoacidcanhaveinsolution,isthepHatwhichitexists
primarilyinitszwitterionform,thatis,itsneutralform(nonetcharge).ThispHvalueisknownastheisoelectric
pointfortheaminoacids.AnisoelectricpointisthepHatwhichanaminoacidexistsprimarilyinitszwitterform.At
theisoelectricpoint,almostallaminoacidmoleculesinasolution(morethan99%)arepresentintheirzwitterion
form.
Every amino acid has a different isoelectric point. Fifteen of the 20 amino acids, those with non polar neutral side
chainhaveisoelectricpointsintherangeof4.86.3.Thethreebasicaminoacidshavehigherisoelectricpoints,and
thetwoacidicaminoacidshavelowerones.Thelistofisoelectricpointsforthe20standardaminoacidsaregiven
below.

Name
isoelectricpoint
alanine
6.01
arginine
10.76
asparagine
5.41
asparticacid
2.77
Cysteine
5.07
glutamicacid
3.22
glutamine
5.65
glycine
5.97
histidine
7.59
isoleucine
6.02
leucine
5.98
lysine
9.74
methionine
5.74
phenylalanine
5.48
proline
6.48
serine
5.68
threonine
5.87

tryptophan
trrosine
valine

5.88
5.66
5.97

ExpandedGeneticCode

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Geneticcodeisthedictionaryofnucleotidebases,whichdeterminesthesequenceofaminoacidsinproteins.The
geneticcode(or)codonshavetripletbasesequencesinmRNA,whichactascodewordsforaminoacids.TheDNA
sequencethatcodeforaspecificprotein(or)polypeptideiscalledagene.Thereare4differentbasesinmRNAA,
G, C and U. They produce 64 different triplets (43). Out of 64 codons 61 codons code for 20 amino acids. The 3
codonsUAA,UAGandUGAdonotcodeforaminoacidsandtheyarecallednonsensecodons. The codons AUG
andGUGarecalledinitiatingcodons.
However,therebeingonly20aminoacids,morethanonecodoncancodeforthesameaminoacid.
Example:CUUandCUCbothcodeforleucine.
Thegeneticcodehasfournoteworthyfeatures
1. Thegeneticcodeisuniversalasthesamecodonscodeforthesameaminoacidinall
livingorganisms
2. Itisdegenerate,i.e.,morethenonecodonscodeforanaminoacid.
3. Itiscommaless.
4. Thethirdbaseofthecodonislessspecific.