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Amino Acids: Structure, Properties
Amino Acids: Structure, Properties
Structure,properties
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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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