|

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.
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.
|

\
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re recunoaste de procesul
chitina
celuloza
hialuronic acid
structural
glicogen depozit
glucoza imediata
energie de principala sursa
ROL

1
2
O
H
3); (n ; O) (H C C. de hidrati
dulce subst. rom sakha zaharuri
dulce glichi glucide
n 2 n
formula
grecesc
grecesc
= >
=
=

=
=
O) C ( CETONICA 2)
O) (-CH A ALDEHIDIC 1)
a carbonilic Grupare
) ( )
) ( ) 1
`]4E=] + ^`
-E=] ^+
GLUCIDE
OZE : trioze
tetroze
pentoze
hexoze
heptoze
cetotrioze
aldotrioze
cetotretoze
aldotetroze
cetopentoze
aldopentoze
cetohexoze
aldohexoze
cetoheptoze
aldoheptoze
OZIDE :
Holozide
Heterozide (heteroglucide sau glicozizi)
Oligozide
Poliozide
diozide (diglucide)
triozide (triglucide)
tetrozide (tetraglucide)
pentozide (pentaglucide)
hexozide (hexaglucide)
etc.
glicogen
amidon
celuloza
etc.

chimica Comp.
re polimeriza de Gr.
C de Nr.
a carbonilic Gr.
OZE : trioze
tetroze
pentoze
hexoze
heptoze
cetotrioze
aldotrioze
cetotretoze
aldotetroze
cetopentoze
aldopentoze
cetohexoze
aldohexoze
cetoheptoze
aldoheptoze
OZIDE :
Holozide
Heterozide (heteroglucide sau glicozizi)
Oligozide
Poliozide
diozide (diglucide)
triozide (triglucide)
tetrozide (tetraglucide)
pentozide (pentaglucide)
hexozide (hexaglucide)
etc.
glicogen
amidon
celuloza
etc.
simple zaharide
simple zaharuri
de monozahari

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.
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.
|

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=
=

|
.
|

\
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=
=

undare sec restul

primare 2 sau 1
) OH ( alcoolice grupari
) O C ( cetonica
) O HC ( aldehidica
a carbonilic grupare

C atomi de nr
cetononoze
aldononoze
nonoze
cetooctoze
aldooctoze
octoze
e cetoheptoz
e aldoheptoz
heptoze
cetohexoze
aldohexoze
hexoze
e cetopentoz
e aldopentoz
pentoze
e cetotetroz
e aldotetroz
tetroze
cetotrioze
aldotrioze
trioze

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a carbonilic grupare
xicetone) (polihidro CETOZE
) xialdehide (polihidro ALDOZE

C
C
CH
OH
O
H
H
2
OH
gliceraldehida
C
CH
2
O
CH
2
OH
OH
dihidroxiacetona
C
C*
CH
OH
O
H
H
2
OH
gliceraldehida
D
C
C*
CH
O
H
H
2
OH
gliceraldehida
HO
-
L
-
STRUCTURA SI IZOMERIA TRIOZELOR
( )
( )
ie enantiomer
rectum R D izomer
istrum sin S L izomer
Fischer prezentare Re =
)
`

=
=
STRUCTURA SI IZOMERIA ALDOTETROZELOR
C
C*
OH
O H
H
OH
C*
H
CH
2
OH
D - eritroza
( E
1
)
C
C
O H
H
C* H
CH
OH
HO
HO
L- eritroza
(E2)
D - tetroza
(T
1
L- tetroza
(T
2
)
)
C
C*
O H
H
OH
C*
H
CH
2
OH
C
C*
OH
O H
H
C*
H
C
2
OH
HO
HO
H
2
zomeri diastereoi izomeri
T E
T E
T E
T E
T T
E E
i enantiomer de perechi 2
2 2
1 2
2 1
1 1
2 1
2 1
= =

)
`

CALCULAREA NR DE STEREOIZOMERI (x)

16 2 x 4, n
8 2 x 3, n
4 2 x 2, n
4
3
2
= = =
= = =
= = =
CALCULAREA NR DE STEREOIZOMERI (x) CALCULAREA NR DE STEREOIZOMERI (x)
|
|
.
|

\
|
=
=
=
asimetrici C de atomi de nr. n
izomeri de nr. x
n
2 x
C
C*
OH
O
H
H
OH
C*
H
C
2
OH
C*
H
C*
OH
H
HO
D - glucoza
C
C*
OH
O
H
H
C*
H
C
2
OH
C*
H
C*
OH
H
HO
HO
D - galactoza
C
C*
O H
H
OH
C* H
C
2
OH
C*
H
C*
OH
H
HO
HO
D - manoza
H
H
H
STRUCTURA SI IZOMERIA ALDOHEXOZELOR

structura
2 pozitia O C functia =

ra nomenclatu
levuloza
xiluloza
ribuloza
" uloza "
|
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|

\
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CARACTERISTICELE GENERALE ALE CETOZELOR

CALCULAREA NR DE STEREOIZOMERI (x)
|
|
.
|

\
|
=
=
=
asimetrici C de atomi de nr. n
izomeri de nr. x
n
2 x
C atom penultimul la de OH pozitia L D, ia configurat
8 2 x 3; n ; cetohexoze
4 2 x 2; n e; cetopentoz
1) (n ; 2 x izomeri nr.de
3
2
n

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\
|
= = =
= = =
< =
C
O
OH
C*
H
C*
H
HO
CH
2
OH
CH
2
OH
C
O
OH
C*
OH
C*
H
H
D-xiluloza
D-ribuloza
CH
2
OH
CH
2
OH
STRUCTURA SI IZOMERIA CETOPENTOZELOR
|
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|

\
|

e =

4
2
C
C
epimeri galactoza D si manoza D
galactoza D si glucoza D
ribuloza D si xiluloza D
exemple
) C (1 deosebire singura 1 izomerie EPIMERIA
REPREZENTANTI semnificatie biochimica
C
O
OH
C*
H
C*
H
HO
CH
2
OH
CH
2
OH
OH
C*
H
C
O
OH
C*
H
C*
H
HO
CH
2
OH
CH
2
OH
OH
C*
H
OH
C*
H
D-fructoza
(sau levuloza)
D-sedoheptuloza
(cetoheptoza)

ARGUMENTE
0
D
0
D
2
5 52 [ glc de veche sol.
2 112 [ glc de proaspata sol.
diferita rotatorie putere
SO cu decolorata fucsina de a recolorare

+ =
+ = |
=
2)
1)
ARGUMENTE ce contravin reprezentarii Fischer
EXPLICATIA
7 52 ] [ amestec anomerie
0
D
+ = o => | , o
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\
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+ =
+ =

7 18 ] [ glucoza D
2 112 ] [ glucoza D
izomeri 2 a existenta
0
D
0
D


ANOMERI

Izomerii
ROTATORII PUTERII SCHIMBAREA
)
`

= E MUTAROTATI
JUSTIFICAREA CHIMICA
R
aldehida
CHO R
+
OH R R
H
OH
alcool
hemiacetal
1
C O
1
Formarea de hemiacetali interni ciclici
C
H
C H
C HO
OH
CH
2
OH
OH
C
H
OH C H
H O
+H
2
O
C
H
C H
C HO
OH
CH
2
OH
OH
C
H
O H C H
H O
OH
- H
2
O
C
H
C H
C HO
OH
CH
2
OH
OH
C
H
C H
H O
O
Forma
aldehida libera
Hidrat de
aldehida
Hemiacetal
Forma glucopiranozica
(punte oxidica 1-5)
Forma liniara
H
1
2
3
4
5
6
REPREZENTARE propusa de TOLLENS
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+
+
furanoza OH) ( aldeh.) 2)(Grup.
piranoza OH) ( aldeh.) (Grup. 1)
HOH
4 1
HOH
5 1
POSIBILITATI de CICLIZARE pt ALDOZE
(GLUCOZA)
O) (5atomi FURAN FURANOZA
O) (6atomi PIRAN PIRANOZA
Etimologia
e
e
CH
2
CH
CH
CH
CH
O
O
CH
CH CH
CH
Structura piranului
CH
2
PIRAN
CH
CH
CH
CH
O
CH
CH CH
CH
Structura furanului
O
FURAN
MODIFICAREA FUNCTIEI REDUCATOARE

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\
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=
acetalica pseudo
ica semiacetal
ica hemiacetal forma O) CH e( reducatoar Funct.
POSIBILITATI de CICLIZARE pt CETOZE
(FRUCTOZA)

|
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+
+
ica hemiacetal
ica semiacetal
nica pseudoceto cetonica functia
) furanozic nucleu ) OH ( ) cetonica . gr .( 2
piranozic nucleu ) OH ( ) cetonica . gr .( 1
HOH
5 2
HOH
6 2

|
o
-
)
`

-
-
izomer
izomer
anomerie C atom acestui OH pozitia
cetoze ) 2 C ( C atom 1 aparitia
aldoze ) 1 C ( C atom 1 aparitia
CONSECINTELE CICLIZARII

e
PIRANOZICA
FURANOZICA
FORMA -

IZOMERI -
GLUCIDELE TOATE

=
oza glucofuran D
oza glucofuran D
oza glucopiran D
oza glucopiran D
amestec a) (sol.apoas Glc

)
`

piranoza
furanoza
HOWARTH
oxidica punte
liniara
TOLLENS

ANOMERIA
RE REPREZENTA
Concluzie

H-C-OH
HO-C-H
H-C-OH
H-C
CH
2
OH
O

H-C-OH
HO-C-H
H-C-OH
H-C
CH
2
OH
O
H OH
HO H

H-C-OH
HO-C-H
H-C
H-C-OH
CH
2
OH
O
H OH

H-C-OH
HO-C-H
H-C
H-C-OH
CH
2
OH
O
H HO
o-D-glucopiranoza |-D-glucopiranoza o-D-glucofuranoza |-D-glucoofuranoza
C
C
C
C
ANOMERII D-GLUCOZEI (reprezentare Tollens)

HO-C-H
H-C-OH
H-C-OH
CH
2
O
OH
CH
2
OH

HO-C-H
H-C-OH
H-C-OH
CH
2
O
OH
CH
2
OH

HO-C-H
H-C-OH
H-C
CH
2
OH
O
OH
CH
2
OH

HO-C-H
H-C-OH
H-C
CH
2
OH
O
OH
CH
2
OH
o-D-fructopiranoza |-D-fructopiranoza
o-D-fructofuranoza |-D-fructofuranoza
C
C C
C
ANOMERII D-FRUCTOZEI (reprezentare Tollens)

H-C-OH
HO-C-H
H-C-OH
H-C
CH
2
OH
O
H
OH
C
sau
CH
2
OH
C O
H
H
OH HO
H
OH
C
C C
C
H
HO
H
sau
CH
2
OH
O
H
H
OH
HO
H
OH
H
OH
H
1
2
3
4
5
6
o-D-glucopiranoza
Transformarea reprezent. Tollens in reprez. Howarth
(alfa-D-glucopiranoza)

H-C-OH
HO-C-H
H-C-OH
H-C
CH
2
OH
O
H OH
C
sau
sau
CH
2
OH
O
H
H
OH
HO
H
OH
H
OH
H
|-D-glucopiranoza
Transformarea reprezent. Tollens in reprez. Howarth
(beta-D-glucopiranoza)

HO-C-H
H-C-OH
H-C-OH
CH
2
O
CH
2
OH
OH
C
sau
O
H
H
OH
HO
H
HO
H
OH
1
2
3
4
5
6
CH
2
OH
H
o-D-fructopiranoza
Transformarea reprezent. Tollens in reprez. Howarth
(alfa-D-fructopiranoza)

HO-C-H
H-C-OH
H-C
CH
2
OH
O
OH
C
CH
2
OH
O
H OH
HO
H
H
OH
1
2
3
4
5
6
CH
2
OH
sau
HOH
2
C
o-D-fructofuranoza
Transformarea reprezent. Tollens in reprez. Howarth
(alfa-D-fructofuranoza)

HO-C-H
H-C-OH
H-C
CH
2
OH
O
OH C
CH
2
OH
sau
CH
2
OH
O
H
OH
HO
H
H
OH
1
2
3
4
5
6
HOH
2
C
|-D-fructofuranoza
Transformarea reprezent. Tollens in reprez. Howarth
(beta-D-fructofuranoza)

H-C-OH
H-C-OH
H-C
CH
2
OH
O
OH
C
H
sau
O
H OH
H
OH
H
OH
1
2 3
4
5
HOH
2
C
O
HOH
2
C
sau
H
o-D-ribofuranoza
Transformarea reprezent. Tollens in reprez. Howarth
(alfa-D-ribofuranoza)
O
O
Forma baie
Forma scaun

=
SCAUN forma
BAIE forma
IE CONFIGURAT plan hexagonal Ciclul
CONFIGURATIA BAIE-SCAUN
H
OH
HO
H
H
OH
OH
CH
2
OH
H
O
H
H
OH
HO
H
H
OH
H
CH
2
OH
H
O
OH
o - glucoza |- glucoza
CONFIGURATIA BAIE-SCAUN pt GLUCOZA
(

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hidroxilic O un pierd care oze deoxioze

manoza D
xiloza D
galactoza D
glucoza D
de monozahari
HO - H
2
C
5
O
H
H
OH
OH
OH
H
H
1
2 3
4
HO - H
2
C
5
O
H
H
H
OH
OH
H
H
1
2 3
4
b - D - riboza b -2-deoxi - D - riboza

derivati
) acetilata (
2
NH ) 2 C ( OH inlocuirea
CH
2
OH
O
H
H
OH
HO
H
OH
H
NH
2
H
D-galactozamina
CH
2
OH
O
H
H
OH HO
H
OH
H
NH-C-CH
3
H
O
N-acetil-D-glucozamina
H - C - OH
HO - C - H
H - C - OH
H - C -OH

HO
O
C
HO O
C
Acid
D-glucuronic

derivati
COOH OH rea transforma
Definiie = lactona acidului 2,3-endiol gulonic
orbic dehidroasc L acid ascobic L acid
oxidare

}
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=
=

+

orbic dehidroasc mono L acid
liber radical
redox sistem
orbic dehidroasc L acid
ascorbic L acid
BIOCHIMICE FUNCTII

Acid
L-ascorbic
O = C
H - C
HO - C - H
CH
2
OH
HO - C
HO - C

O
O = C
H - C
HO - C - H
CH
2
OH
O = C

O
Acid
dehidro-
L-ascorbic
O = C
OH
H OH
OH
OH
OH
OH
H
H
H
H
H
Mioinzitolul (Hexa-alcool derivat de la ciclohexan)