CC DNG BI TP V AMINO AXIT

Dng 1. Bi tp i cng: Cc khi nim- ng ng- ng phndanh php- im ng in- tnh cht vt l.
Bi 1: Da vo ng thc Henxon Hatxenban ngi ta c th xc nh
c t l hm lng aa dng proton ha H2A+, dng ion lng cc HA
v dng proton ha A- :
lg

[ HA]
[ H 2 A]

= pH- pKa1

lg[ A-]/[HA] = pH pKa2

Hy xc nh phn trm hm lng glyxin dng proton ha khi pH=

1,54 v dng proton khi pH = 10,0. Bit pKa1 = 2,35; pKa2 = 9.78.
/s: Ti pH = 1,54 :
lg

[HA]
[H2A+]

= pH - pKa1 = 1,54 - 2,35 = - 0,81

[H2A+]

= 6,46

% [H2A+] =86,59%

[HA] = 13,41%

[HA]

Ti pH = 10,0 :
lg

[A][HA]

= pH - pKa2 = 0,22
[A][HA]

= 1022

% [A]-

62,41 %

[HA] = 37,59%

Bi 2: Gi tn cc gc axit sau :
a. H2NCH2COO-

d. CO-[CH2]2-CH(NH2)-COOH

b.( CH3)CHCH(NH2)COO-

e. H 2N-CO-[CH2]2-CH(NH2)-

COOc. HOOC-[CH2]2- CH(NH2)-COO(/s: a. Glyxyl

b. Valyl c.

g. HO-CH2-CH(NH2)-COO-

- glutamyl d. - glutamyl e. Glutaminyl. g. Seryl).

Bi 3: a. Vit phng trnh cn bng phn li ca axit glutamic.

b. Tnh im ng in.
/s: a.

COO-

COOH
CHNH3

OH-

H+

(CH2)2

COO-

OH-

CHNH3+

CHNH3+

H+

(CH2)2

CHNH2

H+

(CH2)2

(CH2)2
COO-

COO-

COOH

COOH

COO-

OH-

b. pHI = 3,22.
Dng 2. Bi tp vit chui phn ng :
Bi 1: T axit acrylic hy vit PTHH tng hp :
a. Axit - aminopropionic ; b. Axit - aminobutiric.
s: a.
CH2=CH- COOH

OH -

CH 2=CH- COO -

H 2N CH2CH 2- COONa

H+

NH3
O/OH -

H 2N CH 2CH 2- COONa

H2
H 2NCH 2CH 2COOH

b.
CH2=CH- COOH

OH-

CH2=CH- COO

1. H2/Pd
2. H3O+

NaCN

H2O/OH-

CH2CH2- COO-

H2NCH2 CH2CH2- COOH

Bi 2: Hon thnh dy phn ng sau:

Kaliphtalimit

/s:

BrCH(COOEt)2

(CH2) 3Br 2
NaOEt

Kali axetat
B

1. NaOH,t0
2.H+, t 0

HCl
E

Prolin

O
NK
O
O

2. H+, t0

Br(CH2)3Br

NCH(COOEt) 2
O

KOAc

COOEt
C-CH
N
2CH2CH2Br
COOEt
O

1. NaOH,t0

BrCH(COOEt) 2

COOEt
C-CH
N
2CH2CH2OAc
COOEt
O

HCl

NH3 HC-CH2CH2CH2OH
COO-

NH3+ HC-CH2CH2CH2Cl

Prolin

COO-

Bi 3: Hon thnh cc s chuyn ha sau

NH4Cl, KCN

a . m,p-(HO) 2C6H3-CH2CHO

b.n-propylamin

H 2O

NaNO 2/HCl

H3O+

CuO, t 0

B.

1.NH 3

H 3O+

2.HCN

c . (CH3)2CHCH2COOC2H5
d . CH2= CH-CH3

HOCl

Br2/P do

KCN

Kaliphtalimit

HBr

H3O+
NH 3

C + axit phtalic.
H3O+

/s.
a. m,p-(HO) 2C6H3-CH2CHO

b. CH3CH2CH2NH2
1.NH3
2.HCN

NH4Cl, KCN
H 2O
H3O+

NaNO2/HCl

. m,p-(HO) 2C6H3-CH2CH(NH2)CN
A

. m,p-(HO)2C6H3-CH2CH(NH2)COOH

CH3CH2CH2OH

CH3CH2CH(NH2)CN

H 3O+

CuO, t 0 CH CH CHO
3
2
CH3CH2CH(NH2)COOH

c. (CH3) 2CHCH2COOC2H5

Br2/P do

(CH3) 2CHCHCOOC2H5

A
Br
(CH3)2CHCHCOOH + C2H5OH + axit phtalic.

1. Kaliphtalimit
2. H3O+

NH2
d. CH2=CH-CH3

HOCl

CH2-CH-CH 3
Cl

CH2-CH-CH3
CN Br

NH3

KCN

CH2-CH-CH3

HBr

CN OH

OH

CH2-CH-CH3

H3 O+

CH3CH-CH2-COOH
NH2

CN NH2

Dng 3. Bi tp iu ch :
Bi 1: Tng hp cc - aminoaxit sau t cc axit cacboxylic tng ng
a. Alanin.

b. Phenylalanin.

c. Valin

Bi 2: . T ietyl - bromomalonat, kaliphtalimit v cc ha cht v c

cn thit khc hy tng hp cc - aminoaxit sau y (phng php
Gabriel):
a. Leuxin.

b. Phenylalanin

c. Alanin.

Bi 3: . Bng cch kh ha cc axit - oxocacboxylic RCOCOOH trong

hn hp NH3/NaBH4 ngi ta c th tng hp c cc - aminoaxit
(phng php amin kh). S dng phng php trn, hy tng hp glyxin
v alanin t cc axit - oxocacboxylic tng ng.
Dng 4. Bi tp nhn bit :
Bi 1: Dng giy qu v mui nitrit nhn bit cc cht trong cc l sau:
1. CH3NHCH(CH3)COOH;
3. H2NCH2CH2CH2CH(NH2)COOH;

2. HOOCCH2CH(NH2)COOH.
4. H2NCH2CH2COOH.

Hd gii: - Giy qu chuyn mu nhn ra. HOOCCH2CH(NH2)COOH.

- Giy qu chuyn mu xanh nhn ra. H2NCH2CH2CH2CH(NH2)COOH;

- Giy qu

khng chuyn mu

gm:

H2NCH2CH2COOH v

CH3NHCH(CH3)COOH. Dng NaNO2/HCl (c to kh N2

nhn

aminoaxit bc 1, khng to kh nhn ra aminoaxit bc 2).

Bi 2: Dng cc phn ng n gin phn bit cc cht sau :
1. H2NCH2COONH4

2. H2NCH2CONH2

3. CH3NHCH(CH3)COOCH3.

4. CH3CONHCH2COOCH3.

5. Bng phn ng ha hc, phn bit cc cht trong tng cp sau :

1. Axit aspartic v axit suxinic.

2. Phenylalanin v tyrosin.

3. Serin v threonin.
Dng 5. Bi tp tch cc cht ra khi hn hp :
Bi 1: a. Tm gi tr pH in di aspartic, threonin v histidin.
b. C th tch lysin (pHI = 9,6) v glixin (pHI = 5,97) trong dung
dch hn hp bng in di nh th no .
/s: a. Chn pH = 5,6 threonin khng di chuyn v cc no c.
Axit aspactic (pHI=2,77) pH = 5,6 s dng anion chuyn v cc dng
anion.
Histidin ( pHI = 7,59) ) pH = 5,6 s dng cation chuyn v cc m
b. t dung dch mt th xc nh ly pH = 9,6 hoc 5,97 u c
Dng 6. Bi tp tm CTPT v xc nh cng thc cu trc ca hp
cht :
Bi 1: Khi thy phn hon ton mt mol peptit X (tripeptit) thu c 2 mol
axit glutamic
; 1 mol alanin
(HOOC - CH2 -CH2-CH(CH -CHCOOH) ;

NH2

COOH)
NH2

v 1 mol NH3. X khng phn ng vi 2,4-initroflobenzen v X ch c 1

nhm cacboxyl t do. Thy phn X nh enzim cacboxipeptiaza thu c
alanin v mt ipeptit Y.
Xc nh cng thc cu to thu gn ca X, Y v tn gi ca chng.

Bi 2:
NH
(CH3CH2)2N-CH2CH2O C
Novocain l thuc gy t:
2
O
1) Gi tn theo danh php IUPAC.
2) Vit cng thc cu to ca sn phm chnh sinh ra khi cho novocain tc
dng vi :
a) 1 lng tng ng HCl.
b) Dung dch HCl long d, nng.
c) Dung dch NaOH d nng.
3) Cho novocain tc dng vi C6H5SO2Cl to sn phm A tan trong dung
dch NaOH c ngui. Vit phng trnh phn ng v gii thch.
Bi 3:
A l mt axit iamino icacboxylic ngun gc ng vt v c cng thc
phn t C6H12N2O4S2. l 1 ime ca hp cht B c cng thc phn t
C3H7NO2S. Trong phn t B cc nguyn t S v N nh vi cc nguyn t C
khc nhau. Ngi ta c th chuyn A thnh B nh tc dng ca
mecaptoetanol (HO-CH2-CH2-SH). Nu ch ha 1 mol
hepomic (
HACvi
Oaxit
OH
) s thu
O
c mt axit mnh X c CTPT C3H7NO5S.
1) Vit cng thc cu to ca cht A, B v cho bit vai tr ca axit
meaptoetanol
2) Vit cng thc cu to ca cht X gi tr pHI ca n v cho bit gi tr
pHI nm trong khong no (<7; > 7 ; << 7 ; >> 7).
Bi 4:
1) Ion glixin: +NH3 CH2 COOH c pKa = 2,35; 9,78. Hy ghi r gi
tr pKa vo cc nhm.
2) Vit cng thc cu to ca cc tiu phn c mt trong dung dch cha
nc: NH2CH2COOH.
3) Cho bit pH ca dung dch nc cha NH2CH2COOH v tnh t l:
H 3 N CH 2 COO
gi tr pH=4
H 3 N CH 2 COOH

Bi 5:
Ala Asp l 1 ipeptit sinh ra t 1 protein ng vt A, n c gi tr pKa =
2,81; 9,45; 8,6.
1) Vit cu trc lp th ca Ala Asp gi tr pHI , trn ghi cc gi tr
pKa v tr thch hp ? Gii thch. Bit rng:
Asp: axit amino butaioic (HOOC CH CH2 COOH)
NH2

2)Cho Ala Asp tc dng vi: 2,4- initroflobenzen ri un sn phm vi

HCl long. Hy vit s phn ng.
Nu thay 2,4- initroflobenzen bng clobenzen th phn ng c xy ra hay
khng? Ti sao?
Bi 6: Mt peptit vng (A) khi thy phn hon ton sinh ra:
Tyr: p- HO-C6H4 CH2 -CH-COOH
Gly: H2NCH2COOH
NH2

Lys: H2N (CH2)4 CH(NH2)COOH

Phe: C6H5CH2 CH(NH2)COOH
Glu: HOOC(CH2)2CH(NH2)COOH vi s mol bng nhau.
Thy phn khng hon ton A cho: Gly Phe, Lys Gly, Phe Glu. Bit
MA=624g/mol.
Cho A tc dng vi 2,4- initroflobenzen ri cho dn xut em thy phn
th c dn xut 2,4- initroflophenyl ca 1 axit c Mdx = 347g/mol.
a) Xc nh amino axit u N ca A
b) Vit cng thc dng thu gn ca A nu A khng cha vng.
c) A c th c my dng vng, m t cc dng .
d) Vit s tng hp: Gly Phe xut pht t cc amino axit ban u
thch hp.
Bi 7:
Hai cht A v B l ng phn ca nhau c cng cng thc phn t:
C6H13O2N v u c tnh lng tnh. Cho A, B tc dng ring r vi HNO2
sinh ra cht C v D tng ng v u c cng thc phn t C6H12O3. un
nng vi H2SO4: C v D chuyn thnh M v N tng ng c cng cng thc
C6H10O2. Khi b oxi ha: C cho axit oxalic v axit isobutilic cn D cho axit
oxalic v etyl metylxeton.
Vit cng thc cu to ca A, B, C, D, M, N v phng trnh phn ng
xy ra.
Bi 8:
Thy phn hon ton 1 mol polipeptit X cho ta:
2 mol: CH -CH-COOH
3

(Ala) NH
2

1 mol: HOOC (CH2)2 CH(NH2) COOH

1 mol

H2N (CH2)4 -CH-COOH

(Lys)
NH
2

1 mol

CH2 CH-COOH
(His) NH
2

N
H

( Glu)

Nu cho X tc dng vi 2,4- initroflobenzen ( Ar F ) ri thy phn th

c: Ala, glu, lys, v 1 hp cht:
N

CH2 CH-COOH
NH-Ar

N
H

Mt khc thy phn X nh enzim cacboxipeptiaza thu c lys v 1

tetrapeptit. Ngoi ra thy phn khng hon ton X cho ta cacipeptit: Ala
Glu, Ala Ala v His Ala.
1) Xc nh cng thc cu to v gi tn ca polipeptit X.
2) Sp xp cc a.a trn theo th t tng dn pHI.
Bit cc gi tr pHI l: 3,22; 6,0; 7,59; 9,74.
3) Vit cng thc cu to ch yu ca mi a.a trn ti pH = 1 v
13
4) Di tc dng ca enzim thch hp cc a.a c th b ecacboxyl
ha. Vit cng thc cu to ca sn phm ecacboxyl ha Ala
v His.
So snh tnh baz ca 2 nguyn t (N) trong 2 sn phm .
Bi 9:
T tm l loi polime thin nhin m cc monome ca n l 4 loi amino
axit: Glyxin, alanin, serin v tyrosin. Glyxin v alanin chim 75% lng
monome v t l s mol ca amino axit ny l 2:1.
T l v s mol ca serin v tyrosin l 2:3.
1) Tnh t l % s lng ca mi amino axit trong t tm v mol.
2) on mch ngn nht th hin y t l trn gm bao nhiu n v
amino axit
3) C bao nhiu tetrepeptit gm c 4 n v amino axit trn.
Bi 10: Polipeptit A gm aa theo t l Gly, Ala , Val2, Leu2, Ile, Cys4, Asp2,
Glu4, Ser2, Tyr2. A cha mt cu isunfua to vng oeca. A tc dng vi
phenylisothioxianat to thnh dn xut hiantoin ca Glyxin. Mt khc thy
phn A di tc dng ca enzim cacboxypeptiaza thu c axit Aspartic v
mt polipeptit. Thy phn khng hon ton A thu c cc oligopeptit sau :
Cys- Asp
Glu-Cys-Cys Tyr-Cys
Glu-Glu-Cys
Cys-Cys-Ala

Glu-Leu-Glu

Glu-Asp-Tyr

Leu-Tyr-Glu.

Ser-Leu-Tyr

Ser-Val-Cys

Gly-Ile-Val-Glu-Glu.

Hy cho bit trnh t cc aa trong A.

(/s
Gly-Ile-Val-Glu-Glu-Cys-Cys-Ala-Ser-Val-Cys-Ser-Leu-Tyr-Glu-Leu-Glu-Asp-Tyr-cys-Asp ( I )
Gly-Ile-Val-Glu-Glu-Cys-Cys-Ala-Ser-Leu-Tyr-Glu-Leu-Glu-Asp-Tyr-Cys-Ser-Val-Sys-Asp

Cc phn t Cystein c kh nng to cu isunfua- S-S- :

H2N

CH

COOH

H 2N

CH

COOH

CH2

CH 2SH

S
CH 2SH
H2N

CH

S
COOH

CH 2
H2 N

A c cu isunfua to vng oeca nn A l (II) )

CH

COOH

(II)