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Amino Acids

Chapter

Amino acids
Amino acids are the derivatives of carborylic acids

cucH2),cooH
in which at last one hydrogen atom of hydrocarbon side-chain is substituted by amine group

-NH,,
E. g.

c H3-c H (N H2)-CH2-C

H (N

H2)-G HzC OOH

Each amino acid, a component of proteins (except prolire, Pro, and hydroxyproline,) is so
called
cl,-amino acid

This means that to a-C of amino acid are attached -NH, group and side'chain 'R.

RCH(NH2)COOH
23

24

General formula of amino acid

f,P

T,P

R-C-C
.,{". b-

R_C-C

'{",
A

bn

A - neufral brm (wittout electb charge)


B - zwi&rion brm
To

aC

arc atiached amino gn,up and hydrocarbon side+hain

The analyses of vast number of

proteins shown that all proteins are


composed of the 20 ,,standard"
amino acids. These amino acids
are known as c-amino acids,
because, with the exception of
proline, they have primary amino
group on the cr-C. Proline has a
secondary amino group.

a+arborylic amino acids groups lie in a small range around 2.2 so that
above pH 3.5 these groups are almost entirely in their carborylic forms ('COO-).
pK values of the

The o-amino groups all have pK values near 9.4 and are therefore almost entirely in
theirammonium ion forms (-NH,*) below pH 8.0.
This means: ln the physiological pH range, both the carboxylic acid and the amino

groups of a.amino acids are completely ionized forming zrvitterions (or dipolar ions).

Symbolism of amino acids

/,
t

Each protein amino acid is designated by three letters symbol (first three lefiters of
English name) or one letter symbol (first letter of English name). ln the case when more
than one name of amino acids have the same first letter, this letter is symbol of amino

acids morc often found in Proteins.

AminoAcid

3-letters
Symbol

1-lefier
Symbol

3-letters
Symbol

1-letter
Symbol

cysteine

cys

alanine

Ala

histidine

His

glicyne

Glv

isoleucine

lle

leucine

Leu

methionine

Met

proline

Pro

senne

Ser

threonine

Thr

valine

Val

agrinine

Arg

AminoAcid

26

Symbolism of amino acids (c.d.)

Amino Acid

3-letters

1-letter
Symbol

Symbol

1-letter
Symbol

asparaglne

Asn

tryptophan

Trp

asparaginate

Asp

tyrosine

Tyr

phenyloalanine

Phe

selenocysteine

Sec

glutamine

Gln

pyrolysine

Pvl

glutaminate

Glu

asparaglne or

Asx

GIx

AminoAcid

3-letters

Symbol

asparaginate

lysine

Lys

glutamine or
glutaminate

FtF,

Amino Acids with non-polar side-chain


CHs

CH.'
H
I

H-C-NHs*

[=o
'o'

CHs

H-C-CHg

,-l-NHs*
L-o
vr

H-C-NHg"

iro
l

o'

Valine (Val, V)

l-

H-C-H

H-C-CHs
H-E-NHs*

H-C-NHe*

l--o
vr

o'

Alanine (Ala, A)

Glycine (Gly, G)

?"
CHr

H-C-CHa

L--.O
vr

o'

o'

lsoleucine (lle, l)

Leucine (Leu, L)

,-CHA

"1r\c I.H.<2.

(/

NHs'

CHz

t-

H_G_H
I

CHr

H-9-NHs*

H-C-NHg*

).--O
va,

l-

Lo

o'

Va

oPhenylalanine (Phe, F)

Tryptophan (Trp,

Methionine (Met, M)

ItV)

Proline (Pro, P)

28

Amino acids with side-chain bearing electric charge

OH

CHs

HO-CH

QHz

l^

H-9-NHs'

H-9-NHs

L--O
vr,

)^=O
9.,

o'

o'

Serine (Ser, S)

Threonine (Thr, T)

9H,

H-C-NHs*

po
to'

Tyrosina (Tyr, Y)

ooarNHz
O5a-NHz

SH
I

?n,
H-C-NHs*
L---O
v..

o'
Asparagine (Asn, N)

CHz
I

CHr

t-

H_C-H
H-C-NHr*
L--o
va,
I

H-9-NHg*

L-o
va,
o'

(Gysteine (Cys, C)

o'
Glutamine (Gln, Q)

Synthesis of Cystine from two molecules of cysteine


H
+'H3N-=C-a--O
L,o

H
*HrN=-;..<:

CHz

+2H+

CHz
I

SH

cys

CHz

+HgN-C
. -- -'o-pI

,-O

SH

-2H'

CHz

lrz-.1

tr-o
'HsN-C--n, "\O
H

Cystine

cys

30

Amino acids with acidic side-chain

oot'c'
I

9Hz

'HrN-?-.(l\-o
H
Asparaginate (Asp, D)

oooc'
I

?,,
CHz
II
*HrN-t-.<3'
H

Glutaminate (Glu, E)

?1

Amino acids with basic side-chain

NHz

L'.H*
T

NHs*

C:N.
'-\H

CHr

H-N

llCHe
t-

CHz

n?O
-CHt
--?r1".o.

tt-

CHr

CHz

CHz

H-l-NHa*

NHs'

H.N:/N

CHu

H-C-NHs*

[--o

!--o
9r

o'

Histidine (His, H)

oArginine (Arg, R)

Lysine (Lys, K)

32

Amino acids found rarely in proteins


N

SeH
I

9Hz

-8-**r.

ooe{",)

,-rlIl \2

Amino acids Sel i are inserted iltto proteins

CHe

l-

fto
o'

?,,

during biosynthesb

CHr

l-

QHz

Selenocysteine (Sec, U)

H-C-NHg*
L--.o
9a.

o'

Pirolysine (Pyl, O))

Hyp, tlyl i y-carbxsyglutaminate are formed


in course of posttranslated modiffuation of
NHs*
I

CHe

t-

H-C-OH
I

cHz
I

CHe

t-

H-9-NHa'

cro
o'

Hydrorylysine (l-lyl)

oor.ro- ,P
n"lc-c-\o'
I

9Hz

amino acid residues furtroduced in protein chain

Ho---

H-q-NHs*
o--O
I

9a

o'
y-carboryglutaminate

!-+"<:
Hydroryproline (HVp)

33

Amino acids non found in proteins


NHs"

NHs*

NHs*

?,,
?,,
?,,
'HsN-c-H

CHz

t-

?,,

?,,

CHe
l-

t'-o
'o-

9Hz

f=o
'o'

L--a
'o-

y-Aminobutyrate

p-Alanine

Ornithind

-- ,NHz
O \-c
OH

SH

NH

?*,

?,,

9Hz

.l

.nrru-6n

?,,
?,,

CHz

'HsN-cH

L"a
'o'

CHz

f--o
'o-

Homoserine

*HrN-E-,

f'-o
'o-

Homocysteine

Citruline

34

Dependence of amino acid electric charge on medium pH

CHs
I

?'z---..'

?",..^--,

?ra99,

?e9

c-cooH

il

(+1)

PKr = 2,3

ill (-1 )

(0)

PKz = 9,1

35

Change of electric charge of His depends from medium pH

f
6D

t'ce9

oH'

-HC-COOH
nrCr_

HzC.

)=1

\r*-,

Grv*-,

I.

H'

il

PKr = 1,8

(0)

PKz = 6,0

oH'

ll (+1)

(+2)

PKs = 9,2

Hzo

ttr\

i.(o9
-

HzC.

)a

\,N-_H
36

M(-1)

TABLE {-f. Covrr"sxr Srrugrurrs rnn ArrrsvrATroNs oF TlrE'Srrxoeru'Aulxo Acrns or horslNs! THEtr
Occuurrcn, AND THE rf,Vrr,urs oF THEII loxrztnc Groups

Nrnc

Stroctwrl
Symbot Fruulf

Thr*httcr Spbol,

rd

Onelctter

X,ctidoe
tt{r$
(Df

Averegc

Occumc
h hotrinr (%)'

pf,
oCOOH'

pf,

o.NHf r

.lmlao lr:t& nlth mnplolr side cldira

Glycine

Gly

CCIo-

57.0

7.2

9.78

*-l-,
I

NHi

Aleniue

Ala

7l.

COO-

*-J-.n,
I

M{i

Valirc

var
vl\-

l*ucinc

r.eu

QOO-

.CH..
'

NHi

CH'

,-l-/*

COO-

gH.

113.2

.-J,

"-l-.*

Ll\
cH]
NHi
Isoleucinc COO- CH.

Ile
rll

99.1

113.2

,,-l-J-.*.-.".
NHi

Mahioninc CooMet
,-l-ar:-cH.-s-cH,
Ml

131.2

9.28

97.1

r0.64

NHi

H.
Prolinc
pro
cgo- rcf cn.
"..':
-P
n

/'\'''ilH'
Hil
I

Phc ,-J-.r.Jn
Fl\Y

t472

9.3r

Tryptophan

186.2

9.4r

Pbenvlahninc COO-

Nlll

Trp
wl

QOO

*-J-.*.
NHi

p[r
SlIe <'ltrirr

Nln,
ft,:r.kffcrSyabol,
do1;.lr11crSyubot
tdlrr oridt *itl *4d
SniDc Coosc, n-l-cH.-on

sl

I:liir:
Mrt
(D)l

Stnasrl
FcruF
Pter

sl* cblrs

Arcryr

Ooscncc
hhoador(S)'

Pft
aOOHr

Pfr
o-NHi'

rfr
S$cchdo'

trr.l

6.t

2.19

9:l

lOt.t

5.9

2'00

9'10

ll'l.l

4.3

2.11

8'12

128-1

4.3

Z'17

9'13

163.2

3.7

2-20

9-21

t03.t

1.9

1.92

10.70

t28.2

5.9

2.16

9.06

t0-54

(a'NHi)

5.r

1.82

t.99

12.48

Gunidino)

L3

t.t0

9'33

6.Oa

llJ.l

53

t'99

9'90

3'go(pCOOH)

l2g.l

5'3

2.10

9'47

{O7 (}COOH)

NHf

cpo H
,-l-llcH,
NHi oH
AryragrnC COO- O
Aso *-l-.r.-cl
Nl\_'
st
NHi
O
Ouullrinf COO

Tlmoninc

rh
Tll

I Grr u-l-*r.- c'.-t

ol\
-

xHi

NH:

Tvruirrc COO-

r;Y

10'46 (phcnol)

u-J-.r.*4=il-o,
-.\Y

NHi

Gnciac

COO-

;n s-l-*r.-sn
cl

8'37 (sullhvdryl)

NH!-

lldln lrliJl vilt fupn Pobt ti{t clrirl


Lrarc
gooLYr r-6-cHr-cH!-cH!-cH.-liHi

KI

N}li

t562
coo/qH:
tus H-E-cH.-cH.-cH.-NH-q
-'
\
I
R,
"
NHi
*.'
137.1
tlinirlinc ?*
/-x
Hb

tuSioinc

H-c-cH.<
.i

/
.!_..
MIi
H
Artbreid'Ccrr o

:il

,-l-.r.-J
^e
Dl\_
-NH;O
Gbtanicrcid' COo-

ch,
El\^
-NHio

(iuidazob)

38

H-l-cn.-cH.-cl

Summary

1.
2.
3.
.
.
.
.
4.
5.
6.
7.

Amino acids are components of peptides and proteins.


Amino acids participate in formation the catalytic active centens of
enzymatic proteins
Amino acids are precursors in biosynthesis oft
hormones (e.g. adrenaline, tyroxine, histamine, dopamine),
biological pigments (e.g. melanin, hem),
some coenzymes ( e.g. coenzyme A),
neurotransmitters (e.g. acetylocholine and T-aminoacetic acid)t
Amino acids are the substrates for biosynthesis purines nad pirymidinesnucleotides bases.
Fragments of amino acid hydrocarbon skeletons are used in synthesis of
glucose, ketone bodies or are oxidized to HrO and CO2 released ATP cell's energy carrier.
In the cell some amino acids are the sounee of sulfur
Some amino acids participate in biosynthesis of phospholipids.