VITAMINI B KOMPLEKSA

B1, Tiamin
H 3C N N NH 2 S N OH CH 3 Cl

3-[(4-Amino-2-metil-5-pirimidinil)metil]-5-(2-hidroksietil)-4-metiltiazolium-hlorid

Protonovani oblik vitamina B1

H2 N R HN
H 3C N NH2 H 3C N NH2 H N H N

Amidin

CH3 N H OH S H OH N

CH3 N OH S H O

CH3 N OH S H O H HS

CH3

A
OH

CH3 N S O O O CH3 R -H O

CH3 N S OH R HO -CO2 H3 C S N

CH3 +H R H OH N H3C S

CH3

B
R

H3C

Hidroksietil-TPP

O R= CH2 CH2 P O OH O

O P O OH

(A) Nestabilnost u baznoj sredini (B) Mehanizam dekarboksilacije keto kiselina

CH 2OH HO HO HO CH CH CH CH 2 H3C N N NH H3C N

O N HN h, O2 OHO

B2, Riboflavin
Vitamin B2; laktoflavin; vitamin G; 7,8-dimetil-10-(D-ribo-2,3,4,5O tetrahidroksipentil)izoaloksazin;
R N N CH3 CH3 h, O2 H+ H N HN N O CH3 O

O HN

CH3

N N

CH3 CH3

Lumiflavin

Lumihrom

Vitamin B3; Nikotimamid

N NH 2 O

3-Piridinkarboksamid; Prekrsor keenzima NAD i NADP

Vitamin B5; Pantotenska kiselina

OH H N HOOC O H3C CH 3 OH

Vitamin B6; Pirodoksol, piridoksal, piridoksamin

N HO OH OH CH 3

HCl

OH OH HO N H CH3 +H HO N H

OH O + OH CH3

OH O HO + H2O N CH3

pH<7
O H R OH H P O N Aldimin O R OH + H H P O N CH3 NH2 OH CH3 N OH -H P O

pH~7
O R OH H N OH

pH>7
O R OH H P O N CH3 N OH

CH3

O R OH H H OH N +H P O N CH3 Ketimin N H N R

O OH

-ketokarbonska O
kiselina + H2O

OH

CH3

Piridoksamin-5-fosfat (PMP)

Vitamin Bc, Folna kiselina

H2N N N O O H N COOH COOH H N N H N

[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.

CIJANOKOBALAMIN, Vitamin B12

O H2N H3C R CH3 NH2 H2N N H C O 3 H3 C N O Co N CH3 CH3 CH3 H3 C O P O O HO O N H O O N N CH3
N N O

O N NH2

H2 N

R CN = Cianokobalamin CH3 = Metilkobalamin OH = Hidroksikobalamin (12b)

NH2 N N

H3C

NH2

CH3
HO OH

= Adenozilkobalamin (Vitamin B12 koenzim)

O HO

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 (58Co) kapsule i rastvor; +-emiter, t1/2 = 70 dana

BIOTIN
O HN H S NH H COOH H O

Hekshidro-2-okso-1H-tieno[3,4-d]imidazol-4-pentanska kiselina

VITAMIN C, L(+) Askorbinska kiselina

CH2OH HO H H O O [O] [H] HO OH O O HO H CH2OH H O O

pKa1 = 4,1

pKa2 = 11,6

LIPOSOLUBILNI VITAMINI Provitamini: - karoten

CH 3 CH 3 CH 3 H3C H3C

CH 3 CH 3

CH 3

CH 3

CH 3

Vitamin A, retinol
H3 C CH 3 CH 3 CH 3 OH CH 3

CH3
1 2

CH3
3 4

CH3
5

OH CH3 CH3 CH3

5 4 6 7 8

Sistem A CH3
9 10 11 12

(IUPAC)
CH3
13 14 15

OH

CH3
3 2 1

Sistem B

CH3 CH3
9 8 7 6 5 4

CH3

CH3
3 2 1

OH

CH3 CH3

Sistem C

(USP)

Raspoloivi stereoizomeri: all trans; 9-cis; 13-cis; 9,13-dicis;

Stereohemijska zabrana je na C7 i C11

CH3

CH3

CH3 OH

all-(E)-Retinol

CH3 CH3 Retinol dehidrogenaza NADPH CH3 CH3 CH3 H O CH3 CH3 Retinal izomeraza CH3 CH3 NADP

all-(E)-Retinal

CH3 CH3

H 3C H O

4-(Z)-Retinal

Neovitamin A
CH3
5 4 6 7 8

CH3
9 10 11 12

CH3
3 2 1

13

CH3

H3 C
15

14

Tretinoin
CH3 CH3 CH3 O OH CH3 CH3

11-mono-cis-retinol

CH2OH

Retinoinska kiselina
CH3

Izotretinoin
CH3 CH3

CH3 CH3 HO O

13-cis-retinoinska kiselina

SINTETSKI RETINOIDI Etretinat

H3C CH3 CH3 CH3 O O CH3 CH3

H3CO

(all-E)-9-(4-Metoksi-2,3,6-trimetilfenil)3,7-dimetil-2,4,6,8-nonatetraenske kiseline etil estar

CH3 CH3 O OH

Acitretin
H 3C

CH3

H3CO

CH3

(all-E)-9-(4-Metoksi-2,3,6-trimetilfenil)3,7-dimetil-2,4,6,8-nonatetraenska kiselina
CH3 CH3

Leenje: psorijaze i dr. konih oboljenja; antineoplastici; ispoljavaju teratogeni efekat.

Alitretinoin

CH3 CH3

9-cis-retinoinska kiselina

H3C HO O

Vitamin D, Holekalciferol
Provitamini: ergosterol, 7-dehidroholesterol
CH 3 H3C CH 3 H CH 3 CH 3

H3C CH 3 H

CH 3 CH 3

H
H

CH 2
CH 2

HO
HO

Vitamin D2

Vitamin D3

Alfakalcidiol;

(1-holekalciferol)

CH3
21 H3C 18 17 19 8 3 5 6 7 25

CH3 CH3 H3C CH3 H 3C

CH3 CH3

CH3

CH3

CH3

CH2

HO

HO

HO

7-Dehidroholesterol Provitamin D3 h
CH3 H3C CH3

Previtamin D3 h

Vitamin D3

CH3 H3C CH3

CH3

CH3

H
HO

Lumisterol3
(neaktivan)
1

Tahisterol3
(6 trans izomer)
3

OH

SINTEZA
H3C

CH3 CH3 CH3 CH3 H3C CH3 CH3 CH3 H3C CH3 CH3

CH2

HO

HO

CH2

HO

7-Dehidroholesterol

Holekalciferol Vitamin D3
CH3

Holekalciferol

METABOLIZAM
CH3 H3C CH3 CH3 H3C CH3 CH3 OH CH3 H3C CH3 OH CH3

jetra

bubrezi

CH2

CH2

CH2

HO

HO

HO

OH

Holekalciferol

25-Hidroksiholekalciferol Kalcifediol

1,25-Dihiroholekalciferol Kalcitriol

Alfakalcidiol;

(1-holekalciferol)

METABOLIZAM TAHISTEROLA
CH3 H3C CH3 CH3 H3C CH3 CH3 CH3 H3C CH3 CH3 OH CH3

jetra

H3C

H3C

H3C

OH

OH

OH

Tahisterol
OH H3 C CH3

Dihidrotahisterol

25-Hidroksidihidrotahisterol
CH3 H3C CH3 CH3 OH CH3

SINTETSKI VITAMINI D GRUPE

CH2

HO

OH

HO

OH

Kalcipotrien Lokalna primena - psorijaza

Parikalcitol Prevencija hiperparatireoidizma (hronina dijaliza)

Vitamin E, -Tokoferol
CH 3 HO H3C H3C CH 3 O CH 3 H H3C H CH 3 CH 3

Biotransformacija tokoferola
CH3 HO H3C H3C CH3 O CH3 H H3C H CH3 CH3

-Tokoferol

O H3C CH3 CH3 H3C O OH OH H3 C O H3 C

O CH3

O CH3

Tokoferonska kiselina

Tokoferonlakton

VITAMINI GRUPE K
O CH3 CH3 CH3 CH3 CH3 CH3 O

Filohinon (K1)

MENADION, MENADIOL, K5
O CH 3

OH CH3

OH CH3

OH

NH 2

ANTIVITAMINI K VITAMINA (ANTIKOAGULANSI) Derivati kumaruna

O O CH3 OH O

NO 2

OH O

CH3

Varfarin Stereospecifina biotransformacija varfarina

O OH CH2 Ph H
7

Acenokumarol

HO CH3 OH CH2 Ph H O O

H CH3 OH

H CH2 Ph H O O

OH CH3

R-(+)-Varfarin

R,S-(+)-Alkohol Glavni proizvod

R,R-(+)-Alkohol Sporedni proizvod

O OH CH2 H Ph O O CH3 HO
6

O OH CH2 H Ph O O CH3

S-(-)-Varfarin

(S)-6-Hidroksivarfarin

Dikumarini
O O O O

OH O O

OH CH3

Etilbiskumacetat

Bioloka uloga K vitamina u procesu koagulacije

HO O O CH3 HO O O CH3 R O O2 OH CH3 HO OH CH3 O R O O H 2O OH CH3 Reduktaza O CH3 Reduktaza O CH3 O R O Vitamin K oksid H N N H COO COO R COO CO2 O H N N H O O R O Vitamin K baza HO O CH3 O R COO Glutamat H N N H O

R OH Vitamin KH2 O Vitamin K

-Karbokiglutamat

O H N Protein N H O O O Ca Fosfolipidi membrane O O HN Protein O O Protein Protein NH O O Ca O O Protein NH O O HN O Protein