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T E M A 14

OLIGO- i POLIZAHARIDE

1. Dizaharidele.
Dizaharidele reductoare.
Legtura glicozidic (1-4)

-Maltoza.

CH2OH

CH2OH
O

H
H
OH

H
OH

HO

O
H

OH

H
OH

OH

- -D- Glucopiranozil-1,4- -D-glucopiranoza

CH2OH
CH2OH
O H
OH
H
H
O
H
H
OH
H
OH
H C H
O
HO

CH2OH
CH2OH
O H
O H
H
H
H
H
OH
H
OH
H
O
HO
OH
H

OH

OH

OH

Forma ciclic
CH2OH
H
OH

CH2OH

HO

H
H
OH

H
OH

- Maltoza

O
H

OH

Forma-oxo
CH2OH

OH
H

OH

H
+2H2O
H+

H
OH

HO

OH
H

OH

-D-Glucopiranoza

Celobioza
-(1-4)

CH2OH
O

H
H
OH

CH2OH

CH2OH
H
O
H

HO

O
H
OH

H
H

OH

H
OH

OH

(- -D- Glucopiranozil-1,4-glucopiranoza

H
+2H2O
H+

H
OH

OH

HO

H
H

OH

-D- Glucopiranoza

-(1-4)

CH2OH
O
HO
H
O
OH
H
H
H

Lactoza

CH2OH
O H
H
H
OH
H
OH

OH

OH

--D-Galactopiranozil1,4--D-glucopiranoza

CH2OH
O

HO
H
OH

O H

H
O

H
OH

H
H

CH2OH

CH2OH

OH
Lactoza

H
OH

OH

O OH

HO
+H2O
H+

CH2OH

H
OH
H

H
H

OH

-D-Galactopiranoza

O H

H
H
O

H
OH

H
OH

OH

-D-Glucopiranoza

CH2OH
O H
H
H
OH
H 1
HO
O
H
OH
HOCH2 O
H

OH

CH2OH
HOCH2 O OH
O H
H
H2O, (H+)
H
+
H HO
CH2OH
OH
H
H
HO
OH
OH H
H
OH

HO
CH2OH
H

- -D-Glucopiranozil1,2--D-fructofuranozid

-D-Glucopiranoza

-D-Fructofuranoza

Formarea i hidroliza glicozidelor:


CH2OH

CH2OH

O H

H
H
OH

O H

H
H
OH

H
O

HO
H

OH

+ CH3OH

H+

OH
H

OH

Maltoza
CH2OH
CH2OH
O H
O H
H
H
H
H
OH H
OH H
O
HO
OCH3
H

OH

OH

-Metilmaltozid

H2O

Hidroliza glicozidelor n mediul acid


CH2OH

CH2OH

O H

H
H
OH

O H

H
H
OH

H
O

HO
H

OH

CH2OH

H2O,H+

OCH3
H

-Metilmaltozida

OH

O H

H
H
2
OH
HO
H

+ CH3OH

H
OH
OH

-D-Glucopiranoza

Formarea i hidroliza eterilor:


CH2OH
O

H
H
OH

CH2OCH3

CH2OH
H

H
H
OH

H
O

HO
H

NaOH

Maltoza

OCH3
H

OCH3

OCH3

Octametilmaltozida
CH2OCH3

H2O,H+

H
OCH3 H

O
H

OH

CH3 O

OH

OH

H
OCH3 H

CH3I

CH2OCH3

H
H
OCH3
CH3 O

CH2OCH3
H

OH
H

OCH3

2,3,4,6-tetrametil,D-glucopiranoza

H
OCH3 H

+
OH

OH
H

OCH3

2,3,6-trimetil,D-glucopiranoza

CH3OH

Conformaia dizaharidelor
HO

OH

CH2OH
O

OH

HO
HO
OH

Maltoza

O
a

CH2OH

Oe

HO

CH2OH

OH
O

HO

O
O

OH
Celobioza

OH

e Oe

CH2OH

2. Polizaharidele
Amidonul (20% Amiloz i 80% Amilopectin)
Legturi glicozidice (1-4)

CH2OH

CH2OH

H
H
OH

O H

H
H
OH

H
OH

H
OH

OH

O H

H
H
OH

O
H

CH2OH

O
H

CH2OH

O
H

OH

Un fragment al macromoleculei de

O
H

amiloz

OH

Un fragment de amilopectin cu o singur ramificaie

(1-4)

(1-4)

CH2OH

CH2OH

O H

H
H
OH

H
H
OH

CH2OH

O
H

H
OH

H
OH

H
OH

OH

CH2OH

O H

H
OH

OH

-(1-6)

O H

H
H
OH

O
CH2

O
H

OH

CH2OH

H
OH
O

OH

CH2OH

O H

O
H

OH

O
H

OH

Hidroliza complet a amidonului


(C6H10O6)n

n H2O

H+

n C6H12O6
-D-Glucoza

Amidon

Glicogenul

CH2OH

(6105)n

+ H3PO4

O H

Fosforilaza

H
OH

(6105 )n-1 +

H
OPO3H2

HO
H

OH

1-Fosfat de glucoz

Celuloza
(1-4)

CH2OH
O
H
H
OH
H

(1-4)

CH2OH
O
H
H
OH
H

H
H

OH

(1-4)

CH2OH
O
H
H
OH
H

H
H

OH

CH2OH
O
H
H
OH
H

H
H

OH

O
H

Un fragment al macromoleculei de celuloz

OH

Dextranii
(1-6)CH2

CH2
O

H
H
OH

(1-6)-

O H

HO

H
OH

(1-6)CH2

CH2
O H
O H
H

O
H
OH

O H

HO
H

OH

OH

H
OH

CH2
O H

OH

OH

O
O

HO

H
OH

HO

CH2
H

O H

H
OH

OH

(1-4)

HO
H

OH

Un fragment al macromoleculei de Dextran cu o singur ravificaie

3. Heteropolizahatidele
Acidul hialuronic
COOH
H
H
OH
H

(1-4)
CH2OH
COOH
(1-3
(1-3) CH2OH
O
O
O
O
H
H
H
H
O
H
H
O
1
1
4 OH
1
1
H
H
H
H
H
H
HO 3
H
HO 3
H
O
O
OH
H
NHCOCH3
H
OH
H
NHCOCH3

Fragment dizaharidic

Fragment dizaharidic

Hondroitin-4-sulfat
COOH
H
H
OH
H

(1-4)
CH
OH
2
HO3S
O
O
O
H
H
O
1
1
4
H
H
H
H 3
H
O
OH
H
NHCOCH3
(1-3

COOH

HO3S
O

O
H
OH
H

H 1
H

CH2OH
O
H

OH

3
H

(1-3)

O
1
H
H
NHCOCH3

Heparina
(1-4)

(1-4)

(1-4)

CH2OSO3H
COOH
CH2OSO3H
O
O H
O
O H
H
H
H
H
COOH
O
H
H
O
H
4 OH H 1
4 OH
4 OH H 1
OH H 1
H 1
O
H
O
H
H

OSO3H

NHSO3H

Fragment dizaharidic

OH

NHCOCH3

Fragment dizaharidic