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Aminoacids

Structure,properties
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1. Structure of amino acids


2. Properties of amino acids:
ionization
hydrophobicity
Aminoacidsarebuildingblocksofproteins;
Proteinsaremostabundantmacromoleculesinliving
cells;
Proteinsareassembledfrom20aminoacidsandthe
sequencedeterminesthepropertiesofindividual
proteins;

Chiralcarbon

Thesidechaindetermines
thepropertiesofaminoacids
(hydrophobicityetc.)

AAsexistasstereoisomerscompoundswiththesame
molecularformulathatdifferinthearrangement
(configuration).Twostereoisomersthatare
nonsuperimposablemirrorimagesexistforeachchiralamino
acid(enantiomers).
19outof20commonaminoacidsarestereoisomers
(exception:glycine)

ThemirrorimagepairsofAAs:
D(dextro;inLatindexter~right)
L(levo;inLatinlaevus~left)
InFischerprojectionshorizontalbondsextendtowardthe
viewer,andtheverticalbondsextendaway

Ionizationofaminoacids:
pKaofCOOHgroup:

1.82.5

pKaofaNH2group:

8.710.7

AtphysiologicalpHAAsarezwitterions(dipolarionswithboth
positiveandnegativecharge).
Thephysicalpropertiesofaminoacidsareinfluencedbytheionic
statesofthecarboxylandaminogroupsandbyionizable
groupsinthesidechains.
Eachaminoacidhaseither2or3pKavalues,andthesevalues
differamongtheaminoacids.Consequently,atagivenpH,AAs
havedifferentnetcharges.

AAsdifferintheRgroup.
TheAAscanbegroupedintoclassesbasedontheproperties
oftheRgroups,inparticularthepolarityortendencyto
interactwithwateratphysiologiocalpH.
Hydropathymeasureofhydrophobicityofaminoacids.

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AromaticaminoacidsabsorbUVlightat280nm.

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