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VITAMINI B KOMPLEKSAB1, Tiamin
N
N NH2H3CS
N
CH3
OH
Cl
3-[(4-Amino-2-metil-5-pirimidinil)metil]-5-(2-hidroksietil)-4-metiltiazolium-hlorid
N
NH3C NH2
H N
NH3C NH2
H
H2N
R
HN
Amidin
Protonovani oblik vitamina B1
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A
B
N
S
CH3
H OH
N
S
CH3
H OH
OH
N
S
CH3
H OH
OH
N
CH3
O OH
HSH
N
S
CH3
R
O
OCH3
N
S
CH3
RH3C
OH
O
O
H- N
S
CH3
R
HO
H3C
-CO2 N
S
CH3
R
OH
H3C
H
+ H
Hidroksietil-TPP
(A)Nestabilnost u baznoj sredini
(B) Mehanizam dekarboksilacije keto kiselina
CH2
CH2O
PO
O
PO
O
OH OH
R =
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RN
N
NH
N
CH2
CHHO
CHHO
CHHO
CH2OH
OH3C
H3C
B2, Riboflavin
Vitamin B2; laktoflavin; vitamin G;7,8-dimetil-10-(D-ribo-2,3,4,5-
tetrahidroksipentil)izoaloksazin;
Lumiflavin Lumihrom
HNN
O
CH3
HN
N N
N
O
O
CH3
CH3
HN
HN N
N
O
O
CH3
CH3
h , O2h , O2
OH-H+
O
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Vitamin B3; NikotimamidN
NH2
O
3-Piridinkarboksamid; Prekrsor keenzima NAD i NADP
Vitamin B5; Pantotenska kiselina
HN
OH
OHHOOC
O H3C CH3
Vitamin B6; Pirodoksol, piridoksal, piridoksamin
N
OH
CH3
OH
HO HCl
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N
OH
CH3
H
HO
OH
N
O
CH3
H
HO
OH
N
O
CH3
HO
OH
+ H2O
+ OH
+ H
pH7
OHO
N
P
H
O
OH
H
R
OHO
N
P
H
O
OHR
OHO
N
P
H
O
OHR
N CH3 N CH3
-
N CH3
N
OH
CH3
O
N
P
H
O
OHR
N
OH
CH3
NH
O
OHR
H + H
N
OH
CH3
O
NH2
P
HH O
O
OH
R
+
+ H2O
Aldimin
KetiminPiridoksamin-5-fosfat (PMP)
-ketokarbonskakiselina
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Vitamin Bc, Folna kiselina
N
H
N
N
NH2N
O
HN
HN COOH
O COOH
[4-[[(2-amino-1,4-dihidro-4-oxo-6-pteridinil)metil]amino]benzoil]-L-glutaminska kis.
N-[p-[[(2-amino-4-hidroksi-6-pteridinil)metil]amino] benzoil]glutaminska kis.
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CIJANOKOBALAMIN, Vitamin B12
N N
NN
CH3
NH2
O
H2N
O
H2N
OH3C
H3C
H2N
OH3C
CH3
CH3
H3C
O
NH2
Co
NH2
O
CH3
R
CN = Cianokobalamin
CH3 = MetilkobalaminOH = Hidroksikobalamin (12b)
R
NN
NH2
Cianokobalamin; -(5,6-dimetilbenzimidazol-1-il)kobamid cijanid;Gastrointestinalna absorpcija: zavisi od Castle-ovog faktora;Cijanokobalamin (57Co) kapsule i rastvor; -emiter, t1/2 = 271 dan
Cijanokobalamin (58
Co) kapsule i rastvor; +
-emiter, t1/2 = 70 dana
NH
O
O
N
N
CH3
CH3
H3C
PO
O
O
HOO
HO
N N
O
HO OH
= Adenozilkobalamin(Vitamin B12 koenzim)
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NHHN
S
O
H H
H O
COOH
BIOTIN
Hekshidro-2-okso-1H-tieno[3,4-d]imidazol-4-pentanska kiselina
VITAMIN C, L(+) Askorbinska kiselina
OHO
CH2OH
O
OHHO
HO
HO
CH2OH
O
OO
H
HH [O]
[H]
pKa1 = 4,1 pKa2 = 11,6
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LIPOSOLUBILNI VITAMINI
Provitamini: - karoten
CH3
CH3
CH3CH3
CH3CH3
CH3
CH3
H3C
H3C
Vitamin A, retinol
OH
CH3
CH3 CH3CH3H3C
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OH
CH3CH3CH3
CH3
CH3
1 2 3 4 5
OH
CH3CH3CH3
CH3
13
4
5
6
7
89
10
1112
13
14
15
Sistem A
Sistem B
(IUPAC)
32
9
8
7
6
5
4
32
1
OH
CH3CH3CH3
CH3
CH3 Sistem C (USP)
Raspoloivi stereoizomeri:all trans;9-cis;13-cis; 9,13-dicis; Stereohemijska zabrana je na C7 i C11
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CH3
CH3
CH3
CH3 CH3
OH
CH3 CH3 CH3
O
H
NADP
NADPH
Retinol dehidrogenaza
all-(E)-Retinol
- -
CH3
CH3
CH3
CH3
CH3
CH3
H3C
OH
Retinal izomeraza
4-(Z)-Retinal
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Neovitamin A
11-mono-cis-retinol
CH3CH3
CH3
CH3
1
2
3
4
56
78
910
1112
13
14
15
H3C
CH2OH
CH3CH3CH3 O
Tretinoin
OH
CH3
CH3
Retinoinska kiselina
CH3CH3CH3
CH3
CH3
HO O
Izotretinoin
13-cis-retinoinska kiselina
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Etretinat
(all-E)-9-(4-Metoksi-2,3,6-trimetilfenil)-
3,7-dimetil-2,4,6,8-nonatetraenskekiseline etil estar
AcitretinCH3CH3CH3 O
CH3CH3CH3
CH3
O
O
CH3
H3C
H3CO
SINTETSKI RETINOIDI
(all-E)-9-(4-Metoksi-2,3,6-trimetilfenil)-3,7-dimetil-2,4,6,8-nonatetraenskakiselina
CH3H3CO
OH
Alitretinoin
CH3CH3
CH3
CH3
H3C
HO O
9-cis-retinoinska kiselina
Leenje:
psorijaze i dr. konih oboljenja;
antineoplastici;
ispoljavaju teratogeni efekat.
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Vitamin D, Holekalciferol
Provitamini: ergosterol, 7-dehidroholesterol
CH3
H3C CH3
CH3
CH3
H
H
CH3
H3C CH3
CH3
H
H
CH2
HO
CH2
HO
Vitamin D2 Vitamin D3
Alfakalcidiol; (1-holekalciferol)
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H3CCH3
HO
CH3
CH3
H3CCH3
HO
CH3
CH3
H3CCH3
CH2
HO
CH3
CH3
h
7-Dehidroholesterol
Provitamin D3
Previtamin D3 Vitamin D3
3
56
7
8
18
19
21
17
25
hh
H3CCH3
HO
CH3
CH3
H
Lumisterol3
H3CCH3
CH3
CH3
Tahisterol3
OH
(6 transizomer)
1
(neaktivan)
3
5
6
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SINTEZA
H3CCH3
HO
CH3
CH3
H3CCH3
CH2
HO
CH3
CH3H3C
CH3
CH3
CH3
CH2
HO
h
7-Dehidroholesterol Holekalciferol HolekalciferolVitamin D3
METABOLIZAMCH3 CH3 CH3
H3CCH3
CH3
CH2
HO
H3CCH3
CH3
CH2
HO
OH
H3CCH3
CH3
CH2
HO
OH
OH
jetra bubrezi
Holekalciferol 25-Hidroksiholekalciferol 1,25-DihiroholekalciferolKalcifediol Kalcitriol
Alfakalcidiol; (1-holekalciferol)
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METABOLIZAM TAHISTEROLA
H3CCH3
CH3
CH3
H3C
OH
H3CCH3
CH3
CH3
H3C
OH
H3CCH3
CH3
CH3
H3C
OH
OH
jetra
Tahisterol Dihidrotahisterol 25-Hidroksidihidrotahisterol
HO OH
CH2
CH3
H3C
OH
Kalcipotrien
HO OH
CH3
H3C
CH3
CH3
CH3
OH
Parikalcitol
Lokalna primena - psorijaza Prevencija hiperparatireoidizma (hronina dijaliza)
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Vitamin E, -Tokoferol
CH3O
CH3
HO
H3C
CH3
CH3
CH3
H HH3C H3C
Biotransformacija tokoferola
CH3
HOCH3H HH3C H3C
O
O
H3C
H3C CH3
OH
CH3
OH
O
O
O
H3C
H3C CH3
OCH
3
O
Tokoferonska kiselina Tokoferonlakton
CH3OH3C
CH3
CH3
-Tokoferol
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VITAMINI GRUPE K
O
O
CH3
CH3
CH3
CH3 CH3 CH3
Filohinon (K1)
MENADION, MENADIOL, K5
O
O
CH3 CH3
OH
OH
OH
NH2
CH3
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ANTIVITAMINI K VITAMINA (ANTIKOAGULANSI)Derivati kumaruna
O O
OH
CH3
O
O O
CH3
NO2
OH
O
Varfarin Acenokumarol
ereospec na o rans ormac a var ar na
O O
OH CH2
PhH
+
O
CH3
O O
OH CH2
Ph
H
CH3
HHO
O O
OH CH2
PhH
CH3
OHH
7
R-(+)-Varfarin R,S-(+)-Alkohol R,R-(+)-AlkoholGlavni proizvod Sporedni proizvod
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O O
OH CH2
HPh
O
CH3
O O
OH CH2
HPh
O
CH3
HO6
S-(-)-Varfarin (S)-6-Hidroksivarfarin
Dikumarini
OH OH
O O
O O CH3
Etilbiskumacetat
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CH3
R
O
HO O O
CH3
R
O
HO OO
CH3
OH
CH3
HO OH
CH3
R
O
O
HO O
O2Vitamin K baza
HN
NH
O
COO
HN
N
O
Glutamat
Bioloka uloga K vitamina u procesu koagulacije
R
O
CH3
R
OH
OH
CH3
R
O
O
CH3
R
O
O
O
R
O
H2O
ReduktazaReduktaza
Vitamin KVitamin KH2 Vitamin K oksid
COO
HN
COO
NH
O
COO
CO2
-Karbokiglutamat
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NH
O
HNProtein
Protein
O
NH O
O
O
HNO
O
Ca
Protein Protein
O O
Ca
Fosfolipidi membrane
HN O NHO
Protein Protein
