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nCO2 + nH2O
(CH2O)n + nO2
Clasificare
oze,
ozide.
Ozele sau monozaharidele sunt compusi care nu pot fi transformati in compusi mai simpli prin
hidroliza
aldoze - polihidroxialdehide
cetoze - polihidroxicetone
Ozidele se transforma in compusi mai simpli prin hidroliza acida sau enzimatica.
Holizidele formeaza, prin hidroliz, numai oze
Heterozidele formeaz, prin hidroliz acid sau enzimatic, una sau mai mult molecule
de oz si un compus neglucidec, numit aglicon sau genin
Holozoidele sunt :
Oligoholozide/oligozaharide, care prin hidroliz formeaz 2-10 molecule de oze :
diholozide, triholozide, decaholozide
Poliholozide : compusi care contin mai mult de 11 molecule de oze. Polizaharidele
naturale sunt compusi macromoleculari, care conin un numr mare de oze
Oze
CH=O
HC OH
H2C OH
CH=O
HC OH 2
H2C OH
CH=O
HC OH 3
H2C OH
H2 C
C
HC
H2 C
CH=O
HC OH 4
H2C OH
CH=O
HC OH
H2C OH
CH=O
HO CH
H2C OH
D(+)-glycraldhyde
L(-)-glycraldhyde
CH=O
HC OH
HC OH
H2C OH
CH=O
HO CH
HO CH
H2C OH
D-Erythrose
L-Erythrose
CH=O
HO CH
HC OH
H2C OH
D-Throse
OH
O
OH 3
OH
CH=O
HC OH
HO CH
H2C OH
L-Throse
CH=O
HC OH
HO CH
HC OH
HC OH
H2C OH
D(+)-Glucose
HO CH2
HO CH
O
OH
CH=O
HC OH
HC OH
HC OH
H2C OH
CH=O
CH2
HC OH
HC OH
H2C OH
D-Ribose
2-Desoxy-D-ribose
CH=O
HO CH
HO CH
HC OH
HC OH
H2C OH
CH=O
HC OH
HO CH
HO CH
HC OH
H2C OH
D(+)-Mannose
D(+)-Galactose
-D-glucofurannose
HO
O
OH
OH
-D-glucopyrannose
OH
OH
HO CH2
OH
=
HO
-D-glucopyrannose
D-glucose
HO
HO
HO
OH
CH
HC OH
O
HO CH
HC OH
HC
H2C OH
CH=O
HC OH
HO CH
HC OH
HC OH
H2C OH
-D-glucopyrannose
HO CH2
HO CH
O
OH
=
-D-glucofurannose
D-glucose
HO CH
HO CH2
HC OH
O
OH
O
HO CH
OH
=
HC OH
HO
HC
OH
H2C OH
D(-)Fructose
OH
CH
HC OH
O
HO CH
HC
HC OH
H2C OH
CH=O
HC OH
HO CH
HC OH
HC OH
H2C OH
HO CH
HC OH
O
OH
HO CH
=
HC
HC OH
OH
H2C OH
H2C OH
C=O
HO CH
HC OH
HC OH
H2C OH
HO
HO
O
OH
OH
-D-glucopyrannose
O
OH
OH
HO CH2
O
HO
H2C OH
C=O
HO CH
HC OH
HC OH
H2C OH
CH2 OH
OH
OH
Fructofurannose
D-Fructose
H
C
C
OH
OH
Fructopyrannose
...
...
...
O H
(b)
(a)
HO
CH2 OH
H
H C O H
C=O
O H
H C=O
H C O H
O
HO
(c)
H C=O
H O C H
...
(d)
CH=O
HO CH
HC OH
HC OH
H2C OH
+ HCN
D-Arabinose
C= N
HC OH
HO CH
HC OH
HC OH
H2C OH
H2O/H+
COOH
HC OH
HO CH
HC OH
HC OH
H2C OH
C= N
HC OH
HO CH
HC OH
HC OH
H2C OH
C= N
HO CH
HO CH
HC OH
+
HC OH
H2C OH
CO
HC OH
O
HO CH
CH
HC OH
H2C OH
[H]
CH=O
HC OH
HO CH
HC OH
HC OH
H2C OH
D-Glucose
CH=NOH
C= N
CH=O
C= N
HC OH
HC OAc
HC OH
HC OH
CH=O
Ag2O HO CH
Ac2O AcO CH
NH3 HO CH
HO CH
NH2OH HO CH
HC OH
HC OAc
HC OH
HC OH
HC OH
HC OH
HC OAc
HC OH
HC OH
HC OH
H2C OH
H2C OAc
H2C OH
H2C OH
H2C OH
D-Glucose
CH=O
HC OH
HO CH
HC OH
HC OH
H2C OH
CH=N NHC6H5
HC OH
HO CH
C6H5NH-NH2
HC OH
-H2O
HC OH
H2C OH
CH=NH
HC NH NHC6H5
C=O
C O H
HO CH
HO CH
HC OH
HC OH
- C6H5NH2
HC OH
HC OH
H2C OH
H2C OH
CH=NH
CH=N NHC6H5
C=O
C=N NHC6H5
HO CH
HO CH
2 C6H5NH-NH2
HC OH
HC OH
-H2O
-NH3
HC OH
HC OH
H2C OH
H2C OH
CH=N NHC6H5
CH=O
H2C OH
C=N NHC6H5
C=O
C=O
HO CH
HO CH
HO CH
Zn
H 2O
HC OH
HC OH
HC OH
CH3COOH
-2 C6H5NH-NH2
HC OH
HC OH
HC OH
H2C OH
H2C OH
H2C OH
CH=O
HC OH
HO CH
HC OH
HC OH
CH2OH
D-Glucose
R NH2
HC NH R
C O H
HO CH
HC OH
HC OH
CH2OH
CH=N R
HC OH
HO CH
HC OH
HC OH
CH2OH
CH=O
HC OH
HO CH
HC OH
HC OH
H2C OH
D-Glucose
CH=N R
HC OH
HO CH
HC OH
HC OH
CH2OH
[O]
COOH
HC OH
HO CH
HC OH
HC OH
H2C OH
Acide D-gluconique
NH R
CH
HC OH
O
HO CH
HC OH
HC
CH2OH
N-glycoside
H2C NH R
C=O
HO CH
HC OH
HC OH
CH2OH
CO
CH OH
O
HO CH
CH
HC OH
H2C OH
D-Glucono-lactone
HO CH
HC OH
O
HO CH
HC OH
HC
H2C OH
-D-glucopyrannose
HO CH
HC OH
O
HO CH
[O]
HC OH
HC
COOH
acide -D-glucuronopyrannosique
CH=O
COOH
COOH
CO
CO
HC OH
HC OH
HC OH
HC OH
HC OH
O
O
HO CH
HO CH
CH
HO CH
HO CH
HNO3
+ HC OH +
HC OH
HC OH
HC OH
CH
O HC OH
HC OH
HC OH
HC OH
HC
H2C OH
COOH
CO
COOH
COOH
D-Glucose
Acide D-glucosaccharique
CH=O
HC OH HNO3
HO CH
CH2OH
L-Throse
CH=O
HC OH
HC OH
CH2OH
D-Erythrose
COOH
HC OH
HO CH
COOH
Ac. L-tartrique
COOH
HC OH
HNO3
=
HC OH
COOH
COOH
HO CH
HC OH
COOH
CH=O
HNO3 HO CH
HC OH
CH2OH
Ac. D-tartrique
D-Throse
COOH
CH=O
HO CH
HNO3 HO CH
HO CH
HO CH
COOH
CH2OH
Ac. msotartrique
CH=O
HCOOH
HC OH
HCOOH
HIO4
HCOOH
HC OH
HCOOH
HC OH
CH2=O
CH2OH
L-Erythrose
HO CH2
HO
OH
OH
HO CH2
OH + CH3OH
HCl
OH
HO
OCH3
OH
HO CH2
+
HO
OH
O OCH3
OH
HO CH2
O
OH
OH
HO
OH
Ac2O
AcO CH2
O
OAc
OAc
AcO
OAc
Oligozaharide/oligoholozide
HOCH2
OH
OH
O
OH
-Maltose
HO
HOCH2
HOCH2
OH
OH
HOCH2
O
O
OH
O OH
OH
HO
OH
OH
-Cellobiose
HOCH2
HOCH2
O
HO
O
O
OH
OH
OH
OH
OH
-Lactose
HOCH2
O
O CH2OH
O
OH
OH
HO
HOCH2
OH
OH
Saccharose
Poliholozide/polizaharide
HOCH2
O
HOCH2
OH
OH
O
OH
OH
O
OH
OH
HOCH2
O
HOCH2
OH
HO O
HO CH2
O
H2C
OH
O
OH
HO CH2
OH
O
OH
OH
O
OH
CH2
CH2
O
HO
OH
HOCH2
O
OH
OH
OH
HO
OH
HOCH2
O
OH
OH
HO
OH
HOCH2
O
OH
CH2
OH
OH
OH
S
OH
ONa
O C SNa H SO
OH
CS2
NaOH
2
4
C6H7O2 OH
C6H7O2 OH
C6H7O2 OH
C6H7O2 OH
-CS2
-H2O
OH n
OH
OH
OH n
n
n -NaHSO4
HOCH2
HOCH2
HOCH2
O
O
O
O
O
O
O
OH
OH
OH
NHCOCH3
COOH
O
O
OH
HOCH2
NHCOCH3
NHCOCH3
COOH
O
OH
O
O
OSO3- OSO-3 NHSO3
O
OSO3-
HOCH2
OH
Heterozide
Dup natura agliconului sunt
O-heterozide
N-heterozide
S-heterozide
C-heterozide
HOCH2
OH
OH
HO
HOCH2
OH
O CH2
OH
HO
OH
O CH C6H5
CN
OH
HO
OH
N
N
N
O
CH2 OH
OH OH
O
O
NHSO3-
Alfa aminoacizi
CH=O
HC OH
H2C OH
COOH
HC NH2
R
COOH
H2N CH
R
D-glycraldhyde
D--aminoacide
L--aminoacide
CH=O
HO CH
H2C OH
L-glycraldhyde
-aminoacizi alcanoici
H2C COOH
NH2
H3C CH COOH
NH2
H3C CH CH COOH
CH3 NH2
Valine, Val (V)
hidroxi -aminoacizi
CH2 CH COOH
OH NH2
Srine, Ser (S)
-aminoacizi cu sulf
CH2 CH COOH
SH NH2
Cystine,Cys (C)
H3C CH CH COOH
OH NH2
Thronine, Thr (T)
CH2
S
S
CH2
CH COOH
NH2
NH2
CH COOH
Cystine,Cys-Cys
-aminoacides aril-alcanoici
Ornitine
CH2 CH COOH
NH2
HO
Phnylalanine, Ph (F)
CH2 CH COOH
NH2
Tyrosine, Tyr (Y)
-aminoacideshetaril-alcanoici i heterociclici
CH2 CH COOH
NH2
CH2 CH COOH
NH2
N
H
Histidine, His (H)
N
H
Tryptophane, Trp (W)
HO
COOH
N
H
Proline, Pro (P)
COOH
N
H
Hydroxyproline, Hyp
Metode de obinere
R CH2 COOH
Br2/PBr3
-HBr
NH3
R CH COOH -NH Br R CH COOH
4
NH2
Br
CO
CO
CO
NK + X CH COOCH3
-KX
R
CO
N CH COOCH3 + H2O
CO
R
H+
R C COOH + NH3 + H2
O
CO
N CH COOCH3
R
COOH
R CH COOH +
NH2
Pt
+ CH3OH
COOH
R CH COOH + H2O
NH2
H+
R CH NH2
R CH=NH2+
R CH NH2
-H2O
OH
H+/OHR CH=NH2+ + CNR CH COOH
R CH CN + H2O
-NH3
NH2
NH2
COOC2H5 Zn+CH3COOH
COOC2H5 HONO
COOC2H5
HO N=C
H2 C
CH3CONH CH
(CH3CO)2O
COOC2H5 -H2O
COOC2H5
COOC2H5
R CH=O + NH3
COOC2H5 H2O
COOC2H5 RX/B
CH3CONH C
CH3CONH CH
R CH COOH
COOC
H
COOC2H5
2
5
R
NH2
O
CH2 COOH (CH3CO)2O
N
-H2O
NH COR
O
Ar-CH=O
-H2O
Ar CH
N
O
Ar CH
N
O
R
O
[H] Ar CH2
N
H2O
O - R COOH Ar CH2 CH NH2
COOH
R
enzyme
R CH COOH + H2O
R CH COOH + R CH COOH
-AcOH
NH Ac
NH Ac
NH2
(R,S)
(S)
(R)
O
NADH/enzyme
HOOC (CH2)2 C COOH + NH3
HOOC
H2/cat
+H2O
CH2=CH COOH
CH3 CH COOH
CH3
NHCO CH3
NH COCH3
(L)
(CH2)2
NH2
CH COOH + H2O
CH COOH + CH3COOH
NH2
(L)
Proprieti
H3N CH COOR
amphion
H2
R
O
N
O
C
CH
Cu
R CH COOH + Cu2+
-2H+
CH
C
NH2
N
O
O
R
H2
H2N CH COOH + R' COCl
R' CONH CH COOH + HCl
R
R
H2N CH COOH
R
H2NCH2COOH
CH3I
-HI
I-(CH3)3NCH2COOH
AgOH
-AgI
HO-(CH3)3NCH2COOH
-H2O
(CH3)3NCH2COO-
H2 O
R CH COOH
-N2
OH
-HCl
O
Cl- H3N CH C Cl + SO2 + HCl
R
O
O
R' CONH CH C O C OR"+ HCl
R
O
COOH H2N
t
R CH
+
CH R
NH2 HOOC
NH
R + 2H2O
R
HN
O
C OH -H2O
NH2 O
H2N CH COOH
R
LiAlH4
N
H
OH
H2N CH CH2 OH
R
R CH COOH
NH2
t, B
[O]
R CH COOH
R C COOH + NH3
NH2
O
R CH=O + NH3 + CO2
R CH COOH + [O]
NH2
O
N CH C O H
-CO2
R
O + H2N CH COOH
-H2O
R
O
OH
N=CH R
H2O
-R-CH=O
NH2 + O
O
O
O
O
O
O
N
-H+
O
O
-
O
etc
N
-
-H2O
O
O-
O
N
Peptide i proteine
..
O: .. C
C N
C
H
..
: O:
C
C=N
C
H
O
C
C N +
C
H
Clasificarea proteinelor
In funcie de rolul biologic, de solubilitate, de compoziie i de carcteristicile structurale
Dup rolul biologic
proteine de strucvtur
biocatalizatori
anticorpi
hormoni
proteine de transport
Dup solubilitate si dup rolul biologic :
proteine fibroasesau structurale, care sunt insolubile
o colagenul
o elastina
o keratina
proteine globulare, care sunt solubile
o albumine
o globuline
o histone
o protamine
Proteinele se clasific dup nartura componenteleor n :
proteine simple, constituite doar din aminoacizi
proteine complexe, conjugate sau heteroproteine. Conin i o parte neproteic, numit
component prostetic, n funcie de natura creia sunt::
o nucleoproteine
o fosfoproteine
o cromoproteine
o glicoproteine
o mucoproteine
o lipoproteine
Structura primar
... NH CH CONH CH CONH CH CO ...
R2
R3
R1
Structura secundar
...
N
H
R
CH
C
O
H
N
....
CH
R
O
C
....
....
C
O
H
N
CH
R
...
R
R
H
O
H
... N C CH N C CH N C CH ...
O
H
R
O
H N
C O .... H N
C O .... H N
C O ...
Structura teriar
Structura cuaternar
Stabilirea structurii primare sa a unor detalii de structur primar
O2N
H2O
ON
F + H2N CH CONH CH COOH
-HF 2
R2
R1
NO2
O2N
H2O
H+
NH CH CONH CH COOH
R2
R1
NO2
S
H2N CH CO ... + C6H5 NH
R2
C6H5 N
R1
N2H4
+ H2N CH COOH
R3
Sinteza de peptide
Condensarea aminoaxcizilor fr activare
H+
NH
R1
PNH CH COOH +
R
NH C=N
PNH CH CO O
R
NH C=N
N=C=N
PNH CH CO O
R
+ H2N CH COOH
R1
Sinteza Merrifield
BOCNH CH COOH + Cl CH2 R
R1
H+
H+
H2O
DCC
H+
Lipide
Triacilgliceroli. Grsimi i uleiuri
R1
R2
R3
H+
O
C O CH2
O
C O CH
O
C O CH2
acid linoleic
Strides
Sunt esteri ai sterolilor (colesterol, lanosterol etc.) cu acizi grai, de exemplu, palmitat de
colesteril.
C15H31 COO
Fosfolipide
Fosfolipide, fosfatide, glicerofosfatide sunt esteri ai glicerolului care conin oun resta cil saturat,
un resta cil nesatuirat i un rest de acid fosforic. Accti compui se numesc acizi alfafosfatidici(1). Rwestul de acid fosforic esterific i un asminoalcool. n funcie de natura acestuia,
exist fosfatidiletanolamine(2), fosfatidilcoline sau lecitine(3) i fosfatidilserine(4).
H2C OOC R1
HC OOC R2
H2C O P OH
O CH2 CH2 NH2
O
2
H2C OOC R1
HC OOC R2
H2C O P OH
OH
O
1
H2C OOC R1
HC OOC R2
CH3
H2 C O P O
O CH2 CH2 N CH3
O
CH3
3
H2C OOC R1
HC OOC R2
H2C O P OH
O CH2 CH COOH
O
NH2
4
Sfingolipide
Sunt derivai de sfingozin (1), 2-amino-octadec-4-en-1,3-diol, cu configuraie E la dubla
legtur. Au rol structural la nivelul sistemului nervos.
H2C OH
HC NH2
HO CH CH=CH (CH2)12 CH3
O
CH3
H2C O P O CH2 CH2 N CH3
CH3
OHC NHCO (CH2)22 CH3
HO CH CH=CH (CH2)12 CH3
H2 C O
CH2OH
OH
HO
OH
Sphingomyline
Crasine (glycolipide)
COOH
2O2
COOH ...
PG
O
OOH
Izoprenoide
terpeni i terpenoide,
caroteni i carotenoide,
steroide
o
o
o
Terpeni i terpenoide
monoterpeni (10C), care se clasific n :
monoterpeni aciclici (cu trei duble legturi),
monoterpeni monociclici (cu dou duble legturi),
monoterpeni biciclici (cu o dubl legtur),
sescviterpene cu 15C;
dierpeni cu 20C ;
triterpeni cu 30C ;
tetraterpeni cu 40C;
politerpeni, compui macromoleculari (cauciuc natural, gutaperca etc.)
Monoterpeni i monoterpenoide : mentol, eucaliptol i camfor
OH
Sescviterpenoide : farnesol
OH
-carotne
CH=O
[O]
[H]
OH
Triterpeni : scualen
...
Caroteni i carotenoide
Licopen
Alfa-caroten
Beta-caroten
Gama-caroten
Steroide
hormoni estrogeni, derivai ai estranului (2)
hormoni androgeni, derivai ai androstanului (3).
Hormoni progestageni i hormoni corticosuprarenali, derivai ai pregnanului (4).
Acizii biliari derivai ai colanului (5).
sterolii(zoosteroli, fitosteroli, micosteroli), derivai de colestan(6).
12
11
1
2
3
10
A
4
18
13
C
8
D
14
15
17
19
16
22
21
23
24
26
25
27
28
H
H
A
H...
H
Gonan, jonction A/B trans (5)
OH
H3C C CH2CO SCoA
CH2CO SCoA
OH
OH
OH
1) H2O
ATP
H3C C CH2 CH2OH
H3C C CH2CO SCoA
H3C C CH2 CH2 OPP
-CO2
-ADP
2) NADPH
CH2CO SCoA
CH2 COOH
CH2 COOH
-H2O
-CO2
-H2O
OPP
OPP
C20
C10
OPP
OPP
OPP
C15
OPP
OPP
OPP
carotenoides, polyterpenoides
steroides
2C15
C30
HO
HO
C15