Gio khoa ha hu c

280
280
Bin son: V Hng Thi







XV. AMINO AXIT
(AMINO ACID, AXIT AMIN, ACID AMIN)



XV.1. nh ngha
Amino axit hay axit amin l mt loi hp cht hu c tp chc m trong phn t c cha
c nhm chc amin (nhm amino, NH
2
) ln nhm chc axit (nhm cacboxyl,

COOH)

XV.2. Cng thc tng qut

(H
2
N)
n
R(COOH)
n
n, n 1

R: gc hirocacbon ha tr (n + n)


(H
2
N)
n
C
x
H
y
(COOH)
n
n, n 1

x 1

y + n + n 2x + 2

Amino axit cha mt nhm amino,
mt nhm chc axit, no mch h : H
2
N-C
n
H
2n
-COOH ( n 1)

XV.3. Cch c tn

- Coi cc nhm NH
2
(amino) nh l cc nhm th gn vo mch cacbon ca
axit hu c
- Tt c amino axit t nhin c tn thng thng (nn thuc lng mt s amino
axit t nhin c trong chng trnh ph thng, nh: glixin, alanin, axit
glutamic, lyzin)

Th d: H
2
N-CH
2
-COOH Glixin (Glycine, Gly)
Glicocol (Glicocoll)

Axit amino axetic

Axit amino etanoic


CH
3
-CH-COOH

Alanin (Alanine, Ala)

NH
2
Axit -amino propionic

Axit 2-amino propanoic


HOOC-CH
2
-CH
2
-CH-COOH Axit glutamic (Acid glutamic, Glu)
NH
2
Axit -amino glutaric

Axit 2-amino pentanioic
Gio khoa ha hu c
281
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H
2
N-CH
2
-CH
2
-CH
2
-CH
2
-CH-COOH Lyzin (Lysine, Lys)
NH
2
Axit ,-iamino caproic

Axit 2,6-iamino hexanoic


HO-CH
2
-CH-COOH Serin (Serine, Ser)
NH
2
Axit -amino--hiroxi propionic

Axit 2-amino-3-hiroxi propanoic


HS-CH
2
-CH-COOH Xystein (Cysteine, Cys)
NH
2
Axit -amino--mercapto propionic

Axit 2-amino-3-mercapto propanoic


C
6
H
5
-CH
2
-CH-COOH Phenylalanin (Phenylalanine, Phe)
NH
2
Axit -amino--phenyl propionic

Axit 2-amino-3-phenyl propanoic


HOOC-CH
2
-CH-COOH Axit aspartic (Acid aspartic, Asp)
NH
2
Axit -amino sucxinic (Acid -amino succinic)

Axit 2-amino butanioic


CH
3
-CH-CH
2
-CH-COOH Leucin (Leucine, Lue)
CH
3
NH
2
Acid -amino--metyl valeric
Acid 2-amino-4-metyl pentanoic

CH
3
-CH
2
-CH - CH-COOH Isoleucin (Isoleucine, Ile)
CH
3
NH
2
Acid -amino--metyl valeric
Acid 2-amino-3-metyl pentanoic

CH
3
-S-CH
2
-CH
2
-CH-COOH Metionin (Methionine, Met)
NH
2
Acid -amino--(metylsulfanyl) butiric
Acid 2-amino-4-(metylsulfanyl) butanoic

CH
3
-CH - CH-COOH Treonin (Threonine, Thr)
OH NH
2
Acid -amino--hidroxi butiric
Acid 2-amino-3-hidroxi butanoic
Tryptophan (Try)
Acid 2-Amino-3-(1H-indol-3-yl)-propanoic
Gio khoa ha hu c
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Bin son: V Hng Thi
2

t





CH
3
-CH - CH-COOH Valin (Valine, Val)
CH
3
NH
2
Acid -amino--metyl butiric
Acid 2-amino-3-metyl butanoic
Tt c amino axit t nhin u thuc loi -amino axit, nhm amino (-NH
2
) gn vo cacbon th 2 (hay
cacbon ) ca axit hu c. Ngoi cc nhm NH
2
, COOH, trong amino axit t nhin cn cha cc nhm
chc khc nh: OH, HS, CO

C khong 20 amino axit cn to protein cho c th, trong c 12 loi c th to ra trong c th, cn 8
loi amino axit cn phi c cung cp t thc phm. Tm loi amino axit cn thit l: isoleucin, leucin,
lysin, metionin, phenylalanin, treonin, tryptophan v valin (isoleucine, leucine, lysine, methionine,
phenylalanine, threonine, tryptophan v valine). Hai amino axit cn thit cho s tng trng cho tr con m
ngi ta cho rng c th tr con cha t tng hp c, l arginin v histidin (arginine v histidine).

XV.3. Tnh cht ha hc
XV.4.1. Phn ng chy
y

(H
2
N)
n
C
x
H
y
(COOH)
n
+ ( x +

4
+
n
+
2
n'
)O
t
0

4

(x+n)CO
2
+ (
y + 2n + n'

2

)H
2
O + n/2N
2

H
2
N-C
n
H
2n
-COOH + (3n/2 + )O
2

Amino axit ng ng glixin
0
(n + 1)CO
2
+ (n + 3/2)H
2
O + 1/2N
2

XV.4.2. Amino axit l cht lng tnh, n tc dng c c axit ln kim
H
2
N-R-COOH + H
+

H
2
N-R-COOH + OH

H
3
N
+
-R-COOH
H
2
N-R-COO

+ H
2
O
Th d:

H
2
N-CH
2
-COOH + HCl



Cl
-
H
3
N
+
-CH
2
-COOH
Glixin Axit clohiric Mui clorua ca glixin
Axit amino axetic Axit metylamoni clorua axetic
H
2
N-CH
2
-COOH + NaOH H
2
N-CH
2
-COONa + H
2
O
Glixin Natri hiroxit Mui natri ca glixin
Axit amino axetic Natri amino axetat
CH
3
-CH-COOH + H
2
SO
4
CH
3
-CH-COOH
NH
2
NH
3
+
HSO
4

Alanin Axit sunfuric Mui sunfat axit ca alanin
2CH
3
-CH-COOH + H
2
SO
4


(CH
3
-CH-COOH)
2
SO
4
2
NH
2
NH
3
+

Alanin Axit sunfuric Mui sunfat ca alanin
2CH
3
-CH-COOH + Ba(OH)
2


Ba(CH
3
-CH-COO)
2
+ 2H
2
O
Gio khoa ha hu c
283
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0
0
0
0


NH
2


NH
2

Alanin
Axit -amino propionic

Bari hiroxit Mui bari ca alanin
Bari -amino propionat


XV.4.3. Amino axit tc dng vi ru to hp cht c mang nhm chc este

H
2
N-R-COOH + ROH kh HCl bo ha H
2
N-R-COOR + H
2
O
Th d:
H
2
N-CH
2
-COOH + C
2
H
5
OH kh HCl bo ha H
2
N-CH
2
-COOC
2
H
5
+ H
2
O
Glixin; Axit amino axetic Ru etylic Etyl amino axetat

Sn phm to ra dng mui, ly sn phm cho tc dng vi amoniac ti to nhm chc amin (-NH
2
)

XV.4.5. Amino axit tham gia phn ng trng ngng, ng trng ngng to
ipeptit, tripeptit,, polipeptit
Th d:
H
2
N-CH
2
-COOH + H
2
N-CH
2
-COOH
t

; Xt

H
2
N-CH
2
-C-N-CH
2
-COOH + H
2
O
O H
Glixin Glixin Nhm chc amit, lin kt peptit
ipeptit Gly-Gly
n H
2
N-CH
2
-COOH
T

N ;t

; Xt

(-NH-CH
2
-CO-)
n
+ nH
2
O
Glixin Polipeptit ca glixin
H
2
N-CH
2
-COOH + H
2
N-CH-COOH + H
2
N-CH
2
-COOH
CH
3

TN

;t

; Xt

H
2
N-CH
2
-CONH-CH-CONH-CH
2
-COOH + 2H
2
O
CH
3

Tripeptit Gly-Ala-Gly
nH
2
N-CH
2
-COOH +nH
2
N-CH-COOH
D

TN

;t

; Xt
(-HN-CH
2
-CONH-CH-CO-)
n
+2nH
2
O


CH
3 CH
3
Glixin Alanin Polipeptit Gly-Ala

Bi tp 157
Vit cc phn ng to cc tripeptit c th c vi hn hp hai amino axit l glixin v
alanin.
S: 8 phn ng

Bi tp 157
Vit cc phn ng to cc ipeptit c th c vi hn hp gm hai amino axit l glicocol
v axit 2-amino propanoic.
S: 4 phn ng

XV.5. ng dng
Gio khoa ha hu c
284
284
Bin son: V Hng Thi
0




Amino axit t nhin l cht c s to nn cc cht protit trong c th sinh vt (ng vt
cng nh thc vt). Nhiu amino axit c dng trong y hc cha bnh, lm thc n
cho c th ngi bnh, nh metionin (CH
3
-S-CH
2
-CH
2
-CH(NH
2
)-COOH) l thuc b
gan. Mui natri ca axit glutamic (monosodium glutamat) c dng lm gia v cho thc
n (bt ngt hay m chnh). Mt s amino axit c dng lm nguyn liu cho vic sn
xut t tng hp (axit -amino enantoic, H
2
N-CH
2
-CH
2
-CH
2
-CH
2
-CH
2
-CH
2
-COOH,

c dng iu ch t enan).
n H
2
N-CH
2
-CH
2
-CH
2
-CH
2
-CH
2
-CH
2
-COOH
T

N ;t

; Xt
[-HN-(CH
2
)
6
-CO-]
n
+ nH
2
O
Axit -amino enantoic T enan (enng)

XV.6. iu ch


Khi un nng protit trong dung dch axit hoc baz, hoc nh tc dng ca cc enzim
(men) nhit thng, cc lin kt peptit b t ra v protit b phn ct thnh cc chui
polipeptit v cui cng thnh hn hp cc amino axit.

Ghi ch
G.1. Amino axit trng thi tinh th rn, khng mu, hu ht ha tan d trong nc. S
d amino axit c nhit nng chy cao v ha tan nhiu trong nc v chng tn
ti dng ion lng cc hay mui ni phn t (nhm COOH, sau khi cho H
+
, mang
in tch m; nhm NH
2
, sau khi nhn H
+
, mang in tch dng).
G.2. Amino axit no cha s nhm chc axit (COOH) bng s nhm chc amin

(NH
2
) c gi l amino axit trung tnh (nh glixin, alanin), khi ha tan trong

nc to dung dch trung tnh, khng lm i mu qi tm. Amino axit no c cha

s nhm chc axit (COOH) nhiu hn s nhm chc amin (NH
2
) c gi l

amino axit axit (nh axit glutamic, axit aspartic), khi ha tan trong nc to dung

dch c tnh axit, lm i mu qi tm ha . Cn loi amino axit no c cha s
nhm chc amin (NH
2
) nhiu hn s nhm chc axit (COOH) c gi l

amino axit baz (nh lizin), khi ha tan trong nc to dung dch c tnh baz, lm

i mu qi tm ha xanh.

Bi tp 158
Phn bit ba amino axit sau y ng trong cc bnh khng nhn: Glixin, Axit glutamic,
Lizin.

Bi tp 158
Nhn bit cc amino axit sau y cha trong cc l mt nhn: Axit aspartic, Lizin v
Alanin.

Bi tp 159
Vit phng trnh phn ng ca alanin vi: KOH; HCl; CH
3
OH c mt H
2
SO
4
m c.
Gio khoa ha hu c
285
285
Bin son: V Hng Thi


Bi tp 159
Vit phng trnh phn ng gia glicocol vi cc cht sau y: H
2
SO
4
(hai phn ng);
Ca(OH)
2
; Ru n-propylic c mt HCl.

Bi tp 160
Vit phn ng trng ngng to polipeptit ng vi cc amino axit sau y:
a. Axit amino axetic
b. Axit -amino caproic

c. Hn hp hai amino axit trn.


Bi tp 160
Vit phn ng trng ngng, ng trng ngng ca cc cht:
a. Alanin
b. Axit 7-amino heptanoic
c. Hn hp hai cht trn.

Bi tp 161 (Sch Ha 12 Ban khoa hc t nhin)
Cho ba cht hu c: H
2
N-CH
2
-COOH, CH
3
-CH
2
-CH
2
-CH
2
-NH
2
v CH
3
-CH
2
-COOH
a. So snh nhit nng chy ca chng. Gii thch.
b. Lm th no phn bit ba dung dch ca mi cht trn.

Bi tp 161
a. Chn nhit nng chy thch hp: 50
0
C; 8
0
C; 297
0
C cho cc cht: Axit n-

butiric; Alanin; ietylamin.

b. Dng mt thuc th hy nhn bit ba dung dch c ha tan mi cht trn ng
trong ba bnh khng nhn.

Bi tp 162 (Sch Ha 12 Ban khoa hc t nhin)
Cho 0,01 mol hp cht A tc dng va vi 80 ml dung dch HCl 0,125M, sau em
c cn th c 1,835 gam mui. Nu trung ha 2,94 gam A bng mt lng va
NaOH, ri em c cn th c 3,82 gam mui.
Xc nh cng thc phn t v cng thc cu to ca A, bit rng l mt -amino axit

c mch cacbon khng phn nhnh.

(C = 12; H = 1; O = 16; N = 14; Cl = 35,5)
S: Axit glutamic

Bi tp 162
A l mt amino axit mch h c mch cacbon khng phn nhnh. Ly 0,1 mol A cho tc
dng vi dung dch NaOH va , sau em c cn dung dch th thu c 16,8 gam
mui. Nu cho 2,92 gam A tc dng va vi dung dch HCl 0,8M, th cn dng 50ml
dung dch HCl. Sau em c cn dung dch th thu c 4,38 gam mui khan.
Xc nh A v c tn A, bit rng A l mt -amino axit v cc nhm chc cch xa

nhau nht.
(C = 12; H = 1; O = 16; N = 14; Cl = 35,5)
S: Lizin
Gio khoa ha hu c
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Bin son: V Hng Thi


Bi tp 163 (Sch Ha 12, Ban khoa hc t nhin)
Khi thy phn 500 mg mt protit, ta ch thu c cc amino axit sau y:
HOOCCH
2
CH
2
CH(NH
2
)COOH 44mg
CH
3
CH(NH
2
)COOH 178 mg
HSCH
2
CH(NH
2
)COOH 48 mg
HOCH
2
CH(NH
2
)COOH 105 mg
HOOCCH
2
CH(NH
2
)COOH 131 mg
(CH
3
)
2
CHCH(NH
2
)COOH 47 mg
H
2
N(CH
2
)
4
CH(NH
2
)COOH 44 mg
Tnh t s mol cc amino axit trong phn t. Nu phn t khi ca protit l 50 000
vC, th s mt xch ca mi amino axit trong phn t protit l bao nhiu?
(C = 12; H = 1; O = 16; S = 32; N = 14)
S: 3 : 20 : 4 : 10 : 10 : 4 : 3; 30 : 200 : 40 : 100 : 100 : 40 : 30

Bi tp 163
Thy phn hon ton 43,3 gam mt polipeptit, ngi ta thu c cc amino axit vi khi
lng mi cht nh sau:
Glixin: 22,5 gam
Alanin: 17,8 gam
Xystein: 12,1 gam
a. Tnh t l s phn t mi loi amino axit c trong polipeptit trn.
b. Nu polipeptit trn c khi lng phn t l 433 vC, hy xc nh s phn t
mi amino axit c trong phn t polipeptit ny.
(C = 12; H = 1; O = 16; N = 14; S = 32)
S: Gly : Ala : Cys = 3 : 2 : 1

Bi tp 164 (Sch Ha 12, Ban khoa hc t nhin)
Hy phn bit cc dung dch sau y bng phng php ha hc: lng trng trng, h
tinh bt, glixerin.

Bi tp 165 (Sch 12, Ban khoa hc t nhin)
Gii thch cc hin tng sau y:
a. Sa ti lu trong khng kh b ng vn to thnh kt ta.
b. Khi b ng c bi ch trong thc n, ngi ta khuyn nn ung ngay nhiu sa.
c. Trong sn xut ng th cng, hay khi lm bnh t ng khng trng, khi
thng nc ng i khi ngi ta cho thm lng trng trng vo v un ln.

Bi tp 166
Hn hp A gm hai amino axit cha mt nhm amino, mt nhm chc axit, no, mch h.
Cho m gam A tc dng hon ton vi 200 ml dung dch HCl 2M (c d), thu c dung
dch B. tc dng ht vi cc cht trong dung dch B cn dng va 250 ml dung
dch NaOH 2,8M. t chy hon ton m gam A, ri cho sn phm chy hp th vo dung
dch NaOH c d, khi lng bnh ng dung dch NaOH tng thm 52,3 gam.
a. Tnh m.
b. Xc nh CTCT mi cht trong hn hp A, bit rng khi lng phn t hai cht
trong hn hp A hn km nhau 14 vC.
Gio khoa ha hu c
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Bin son: V Hng Thi


c. Vit phng trnh phn ng ca amino axit c khi lng phn t nh vi: HCl;
NaOH; CH
3
OH; Phn ng trng ngng to tripeptit; Phn ng trng ngng to
polipeptit.
Sn phm ca hn hp A gm CO
2
, H
2
O v N
2
.
(C = 12; H = 1; O = 16; N = 14)
S: m = 25,3 gam; 29,64% H
2
N-CH
2
-COOH; 70,36% H
2
N-C
2
H
4
-COOH

Bi tp 166 (Sch B tuyn sinh i hc mn ha hc)
Cho a gam hn hp hai amino axit no mch h cha mt chc axit v mt chc amino
tc dng vi 110 ml dung dch HCl 2M, c dung dch A. tc dng ht cc cht
trong dung dch A cn dng 140 ml dung dch KOH 3M.
Mt khc t chy a gam hn hp hai amino axit cho trn v cho sn phm chy qua
dung dch NaOH d th khi lng bnh ny tng thm 32,8 gam. Bit rng khi t chy
nit to thnh dng n cht.
a. Xc nh CTPT ca hai amino axit, bit t l khi lng phn t ca chng l
1,37.
b. Tnh % v s mol ca mi amino axit trong hn hp ban u.
(C = 12; H = 1; O = 16, N = 14)
S: 75% H
2
N-CH
2
-COOH; 25% H
2
N-C
3
H
6
-COOH

Bi tp 167 (Sch Ha 12, Ban khoa hc t nhin)
Vit CTCT v gi tn cc amino axit c CTPT C
3
H
7
O
2
N v C
4
H
9
O
2
N.

Bi tp 168 (Sch Ha Hc lp 12)
Este A c iu ch t amino axit B v ru metylic. T khi hi ca A so vi H
2
l
44,5. t chy hon ton 8,9 gam este A thu c 13,2 gam kh CO
2
, 6,3 gam H
2
O v
1,12 lt N
2
(o ktc).
Vit CTPT v CTCT cc cht A v B.
(C = 12; H = 1; O = 16; N = 14)
S:C
3
H
7
NO
2


Bi tp 169 (Sch Ha Hc lp 12)
Tnh gn ng khi lng phn t ca mt protit cha 0,4% st, nu gi thit rng trong
mi phn t ca protit ch c mt nguyn t st.
(Fe = 56)
S: 14 000 vC

CU HI N PHN XV

1. Amino axit l g? Vit CTCT 4 amino axit v c tn cc cht .

2. Vit CTCT ca : Glixin; Alanin; Axit glutamic; Lyzin v phn loi chng (thuc
amino axit trung tnh hoc amino axit axit hoc amino axit baz)

3. Ti sao ngi ta ni amino axit l mt cht lng tnh. Cho th d bng phn ng
minh ha.
Gio khoa ha hu c
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Bin son: V Hng Thi




4. (TSH khi A, 2003)
A l cht hu c khng phn ng vi Na. Thy phn A trong dung dch NaOH ch to
ra mt mui ca -amino axit (amino axit c mch cacbon khng phn nhnh cha

mt nhm amino v hai nhm cacboxyl) v mt ru n chc. Thy phn hon ton

mt lng cht A trong 100 ml dung dch NaOH 1M ri c cn, thu c 1,84 gam
mt ru B v 6,22 gam cht rn khan C. un nng lng ru B trn vi dung dch
H
2
SO
4
m c 170C thu c 0,672 lt olefin (ktc) vi hiu sut phn ng l
75%. Cho ton b cht rn C tc dng vi dung dch HCl d ri c cn, thu c cht
rn khan D. Qu trnh c cn khng xy ra phn ng.
a) Tm CTPT v vit CTCT ca A.
b) Tnh khi lng cht rn D.
(C = 12; H = 1; O = 16)
S: A: C
9
H
17
O
4
N (ietyl glutamat); 9,52 gam D
(D: mui clorua ca axit glutamic v NaCl)

5. Ti sao c mt s amino axit c gi l cn thit cho c th? l cc amino axit
no?

6. cc nc ngho, nguyn nhn ch yu ca s suy dinh dng l do u? Ti sao tr
con d b suy dinh dng hn so vi ngi trng thnh?

7. Ti sao gi l amino axit axit, amino axit trung tnh, amino axit baz? Mi loi hy
ly mt th d c th minh ho.

8. Ti sao ngi ta ni n qu nhiu cht m trong cng mt lc (nh d m tic hay
m gi) ch lm mt c th ch khng ch li lu di?
9. Vi cng thc phn t C
2
H
5
NO
2
ng vi cc cht nh: nitro etan (CH
3
CH
2
NO
2
);
glixin (H
2
NCH
2
COOH) ; etyl nitrit (C
2
H
5
ONO, este ca ru etylic vi axit nitr);
metyl carbamat (CH
3
OCONH
2
); N-Hidroxi acetamid (HO-NH-COCH
3
). C th nhn
bit glixin nh da vo:
a) Glixin trng thi rn, d ha tan trong nc, c nhit nng chy cao nht
b) Ch c glixin trng thi rn, cc cht khc trng thi lng hay kh
c) Dung dch glixin lm i mu qu tm ha , do trong phn t ca n c mang
nhm chc axit -COOH
d) C (a), (b) v (c)
10. Phn tch nh lng mt cht hu c A c to bi bn nguyn t C, H, N v O,
thu c thnh phn phn trm khi lng cc nguyn t nh sau: 31,44%C;
1,31%H; 18,34%N. Cng thc phn t A cng l cng thc n gin ca n. A l:
Gio khoa ha hu c
289
289
Bin son: V Hng Thi




a)
H
2
NCH
2
COOH
b)
NO
2



c) O
2
N COOH d)



O
2
N

OH

NO
2






(C = 12; H = 1; N = 14; O = 16)
NO
2