Chemistry 2100 Chapter 14. ALCOHOLSETHERSTHIOLS thiol / mercaptan (sulfhydryl) alcoholether.
Glutathione Q. 26. Glu Cys Gly N-terminal C-terminal -glutamyl-cysteinyl-glycine sulfhydryl group...
108
COOH CH 2 NH O SH C CH 2 CH NH 2 O NH C CH 2 CH 2 CH COOH glutathio ne Q. 26. Glu Cys Gly N-terminal C-terminal -glutamyl-cysteinyl-glycine sulfhydryl group amide/peptide bond
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Transcript of Glutathione Q. 26. Glu Cys Gly N-terminal C-terminal -glutamyl-cysteinyl-glycine sulfhydryl group...
COOH
CH2
NH
O
SH
C
CH2CH
NH2
O
NH
C
CH2
CH2
CH
COOH
glutathione
Q. 26.
Glu
Cys
Gly
N-terminal
C-terminal
-glutamyl-cysteinyl-glycine
sulfhydryl group
amide/peptide bond
C
NC
C
S
C
C CH3
CH3
H
H H
NHC
COOH
R
O
O
26. tétel
penicillin
R =CH2
penicillin G penicillin V
OCH2R =
CysVal
-lactam ring
thiazolidine ringpeptide bond
peptide bond
H
H
H2N CH2 CH2 C N
O
H
CH CH2
COOH
C
N
CH
N
C
Q. 26.
carnosin
-alanine hystidine
peptide bond
Q. 27.
-helix
H-bond
The probability of the helical structure is decreased by:
proline, glycine, tyrosine, asparagine
R C H
C
N
C
C
N
CR H
H R
OH
R C H
C
N
C
C
N
CR H
H R
H HO
O
O O
H
RH
HR C
N
C
C
N
C
HCR
O
H
H
R C H
C
N
C
C
N
CR H
H R
O
OH
H
O
O
H
H
HR
N
C
CH R
C
C
N
RH C R C H
C
N
C
C
N
CR H
H R
H
HO
O
-sheet
paralel
antiparalel
H-bond
H-bond
Q. 27.
myoglobin
Q. 27.
hem
O O
OH
H
OH
H
H
O
HH
H
OH H
HOHCH2OH
CH2OHCH2OH
OH
saccharose (sucrose)
glycosidic bond(1→2)
-D-glucopyranosyl--D-fructofuranoside
glucose fructose
1
2
3
4
5
6
1
23 4
5
6
Q. 30.
OH
O
OH
OH
O
H
OHGlü 1
23
4
5
6
reducing
O OHH
H
HH
H
O
HOHOH H H
OH OH
OH
CH2OH CH2OH
H
OH
glycosidic bond(1→4)glucose
4--D-glucopyranosyl--D-glucopyranose
Maltose
glucose
1
23
4
5
6
Q. 30.
O
OHH
H
H
OOH H
OH
OH
CH2OH
HH
OH
OHH
H
H
CH2OH
OH
glycosidic bond(1→4)
glucosegalactose
lactose
4--D-galactopyranosyl--D-glucopyranose
O
OH
OH
OH
OH
O
OH
OH
OH
OH
O
1
23
4
5
6
1
23
4
5
6
Q. 30.
O
H
H
HO H
O H
C H 2 O H
H O
OH
H
H
O H H
O H
O H
C H 2 O H
H
O
H
H
glycosidic bond(1→4)
glucose glucose
cellobiose
4--D-glucopyranosyl--D-glucopyranose
OH
O
OH
OH
O
H
OHGlü 1
23
4
5
6
reducing
Q. 30.
OOO
OHOH
OH
OOH
O
OH
OH
OO
OHOH
OH
Cellulose
-D-glucose -D-glucose -D-glucose
glycosidic bond(1→4)
H-bond
H-bond
Q. 31.
O
CH2OH
H
O
CH2OH
O
O
CH2OHO
O
O
CH2OHO
HOH2C
O
O
O
HOH2C
O
HOH2CO
O
OHO
HO
O O
HO
O
H
O
O H
O
OH
H
OO
HH
H
HH
O
O
HH
31. tétel
amylose
glycosidic bond(1→4)
monomer: glucose
dimer: maltose
n
H
O
H
O
O
H
H
H
H
CH2OH
HO
O H
H
HHOH H
OH
CH2OH
OO
OH
H
OH H
OH
OHH
O
CH2
O
OH
H
OH H
OH
CH2OH
H
O
HO H
H
HHOH H
OH
CH2OH
O
amylopectine
glycosydic bond(1→4)
-D-glucose
Q. 31.
H
COOH
H
OH
HOHH
H
H
O
O
H
OH
H
H
CH2OH
H
O
NHCOCH3
OO
n
-D-glucuronic acid N-acetyl--D-glucoseamine
hyaluronic acid(glycosaminoglycal)
(1→3)(1→4)
Q. 31.
chondroitin-6-szulphate
-D-glucuronic acid N-acetyl--D-glucoseamine-6-sulphate
COOH
H
OH
HOHH
H
H
O
O
n
O
H
H
H
NHCOCH3
H
OO
H
O
CH2OSO3H
H
(1→3)(1→4)
Q. 31.
nH
O OHH
HH
H
O
HOHOH H HH
COOH
NSO3HOSO3H
O O
H
CH2OSO3H
heparin
-D-glucuronic acid-2-sulphate N-sulpho--D-glucoseamin-6-sulphate
(1→4)
Q. 31.
oleic acid
Q. 31.
C O O H
C H 2
C H
C H
C H 2
C H 3
7
7 COOH
Z
9
1
linoleic acid
Q. 31.
C O O H
C H 2
C H 2
C H
C H
C H 2
C H 3
6
4
2
COOH
Z
Z
1
9
12
linolenic acidall-cis
Q. 31.
3
C O O H
C H 2
C H 2
C H
C H
C H 2
C H 3
6
4
3
3
C O O H
C H 2
C H 2
C H
C H
C H 2
C H 3
ALA GLA
COOH
COOH
ALA GLA
1
912
15
1
9
12
15
6
COOH1
2
3
456
789
10
11 12 14
arachidonic acid
eicoza-5,8,11,14-tetraenic acid
cis
Q. 33.
O
CH3
OHHO
COOHZ
E
prostaglandin E2 (PGE2)
secondary, alcoholic OH
carbonyl group
Q. 33.
prostaglandin A2 (PGA2)
Q. 33.
O
OH
COOHZ
E
secondary alcoholic OH
carbonyl group
phosphate ester
CH2 O P
O
OH
OH
CHOCR2
O CH2 O C R1
O
glycerol
ester bond
fatty acid
phosphoric acid
glycerophospholipides
Q. 33.
C O C
CHOC
NH2CH2CH2OPOC
O
O
O
OH
H2
H2
ethanolamine
stearic acid
linoleic acid
L--cephalin
phosphatidyl-ethanol-amine
Q. 33.
H2
H2 O P O CH2 CH2 N CH3
O
O
CH3
CH3
C CO
O
O
C O CH
C
stearic acid
linoleic acid
choline
lecithin
phosphatidyl-choline
Q. 33.
H2
H2 O P O CH2 CH COOH
O
OH NH2
C CO
O
CHOC
O
C
serine
phosphatidyl-serine
Q. 33.
C CO
C O CH
C
O
O
OH OH
OHOH
OH
O P O
OH
O
H2
H2
inositol
phosphatidyl-inositol
Q. 33.
H3
H3
HO
C
CCH3
CH3
H
H CH3
HCH3
A B
C D
ergosterol
secondary,
alcoholic OH
-directed
double bonds
Q. 34.
HO
vitamin D2
methylene group
secondary,
alcoholic OH
-directed
Z
Q. 34.
HO
vitamin D3
methylene group
secondary,
alcoholic OH
-directed
Q. 34.
CH3
OH
CH3
OH
COOHOH
CH3H
steric structure of cholic acid
3,7,12-trihydroxy-cholanic acid
A
B
C D
-directed hydroxyl groups
trans
cis
ring junction:
1
2
34
56 7
8910
11 12 13
1415 16
17
18
19
Q. 36.
CH3
CH3OH
O
H
testosterone
17-hydroxy-4-androstene-3-on
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
carbonyl group
secondary,
alcoholic OH
-directed
ring junction:B/C , C/D trans
A B
C D
Q. 37.
CH3O
OH
H
estrone
A B
C D
carbonyl group
phenolic OH
ring junction:
B/C , C/D trans
aromatic ring
base skeleton: estrane
Q. 37.
estradiol
1,3,5(10)-estratriene-3,17-diol
CH3OH
OH
HA B
C D
secondary
alcoholic OH
phenolic OH
ring junction:
B/C , C/D trans
aromatic ring
base skeleton: estrane
stilbene
Q. 37.
CH3
O
H
CH3
CH3
O
progesterone
4-pregnene-3,20-dione
base skeleton: pregnene
acetyl group
carbonyl group
Q. 37.
CH
O
H
CH3
CH2OH
O
OH
O
aldosterone
carbonyl group
carbonyl group
hydroxymethyl
group
hemiacetal formation
1
3
4
5
1711 13
formyl group
secondary
alcoholic OH
Q. 37.
CH
O
H
CH3
CH2OH
OOH
Ohemiacetale
aldosterone
Q. 37.
CH3
O
H
CH3
CH2OHO
OHOH
hydrocortisone or cortisol
11,17,21-trihydroxy-4-pregnene-3,20-dione
carbonyl group
tertiary
alcoholic OH
-directed
17
Q. 37.
anellation of rings:
A/B, C/D cis
B/C trans
CH3
OH
OH
CH3
O O
H
digitoxigeninsecondary
alcoholic OH
-directed
tertiary alcoholic OH
-directed
A B
C D
-unsatureted
lactone ring
3 5
10
13
14
17
Q. 38.
CH3
OH
OH
CH
O O
OH
O
anellation of rings:
A/B, C/D cis
B/C trans
strophantidinsecondary
alcoholic OH
-directed
tertiary alcoholic OH
-directed
-unsaturated
lactone ring
3 5
10
13
14
17
Q. 38.
CH3
CCH2
CH2H2C
O P
O-
O
O P
O
O-
O-
IPP
isopentenyl pyrophosphate
Q. 39.
ester bondanhydride bond
limonene
Q. 39.
h
t
geraniol
CH3
CCH3H3C
CH2OHhead
tail
1
2
3
4
5
6
7
8
primary
alcoholic OH
Q. 39.
camphor
4
H3C CH3
O
CH3
CH3
C CH3H3C
O2
35
6
7
8 9
1
10
O
CH3CH3
CH3
1
23
4
5 6
7
8 9
10
H3C CH3
O
CH3
CH3
C CH3H3C
O
1
2
3
45
6
7
8 9
10
*
*
*
*
*
*
Q. 39.
phytol
CH2OH
tail
head head head
tailtail
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
unsaturated primary alcohol
Q. 39.
vitamin A
all-trans
CH2OH
-ionone ring
primary alcohol
hth
Q. 39.
squalene
h
t t t
ttt h
h h
Q. 39.
-carotene
all-trans
12
3
45
6
7
8
9
10
11
12
13
14
15
1617
18
19 20
1’
2’
3’
4’5’
6’7’
8’
9’
10’
11’
12’
13’
14’
15’
16’17’
18’
19’20’
-ionone ring
Q. 40.
-carotene
all-trans
-ionone ring
-ionone ring
Q. 40.
lycopene
all-trans
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17 18 19
15’
20
19’
1’
2’
3’
4’
5’
6’
7’
8’
9’
10’
11’
12’
13’
14’
16’
17’
18’
Q. 40.
zeaxanthin
all-trans
HO
HOH
H
alcoholic secondary OH
*
*
Q. 40.
Q. 40.
Vitamin A
all-trans
CH2OH
-ionon ring
primary alcohol
flf
N
H
OH
indoxyle
Q. 42.
indole ring
serotonin
N
HOCH2
CH2
NH3
H
+
phenolic OH
indole ring
Q. 42.
papaverine
N
CH3O
CH3O
CH2
OCH3
OCH3
isoquinoline ring
methylene group
benzyl group
methoxy group
Q. 42.
quinine
N
CHOHN
CH2
CH2
CH CH2
CH3O
quinoline
quinuclidine
vinyl group
*
*
*
*
secondary alcoholic OH
Q. 42.
methylene blue
N
S NN
CH3 CH3
CH3H3C +
Cl
tiazine
aromatic quinoidal
dimethylamino
group
dimethylimino
group
Q. 42.
uric acid
2,6,8-trihydroxy-purine
N
N NH
N
OH
OH
OH
NH
N NH
N
O
OH
OHNH
NH
NH
NH
O
O
O
enolic OH
acidic
purine1
2
3
4
78
9
5
6
carbonyl group
trilactime
dilactime lactame
Q. 42.
HEME
protoporphyrine IX-Fe-complex
NH3C
CHCH2
N
CH3
CH CH2
N
H3C
HOOC COOH
CH3
N
Fe IIwithout iron: porphine methyne group
pyrrole ring
carboxyethyl group
vinyl group
Q. 43.
bilirubin
HN
H3C CH
CH2
O C N
H3C CH
CH2
OHHH H
B C D A
H
CH2
COOH
C
N C
CH3
HH
C
H3C
COOH
CH2
CH2
N
H2
carbonyl groupmethyne groupmethylene group
pyrrole
carboxyethyl group
vinil group
Q. 43.
H2
ADCB
HH H HN O
H3C CH
CH2
NO
CH
CH2
H3C
CH
H3C
N
CH2
CH2
COOH COOH
CH2
C
C
CH3
CNH
biliverdin
carbonyl group methyne groupmethyne group pyrrole
carboxyethyl group
vinyl group
Q. 43.
Mg
NH3C
CHCH2
N
R
CH2 CH3
CH3
N
OH3COOC
N
H3C
O
O
chlorophyll
without Mg: porphyrine methyne group
pyrrole ring
vinyl group
ester bond phytol
Q. 43.
hypoxanthine
6-hydroxy-purine
1
2
3
4
7
8
9
5
6
N
N N
NH
OH
NH
N N
NH
Ophenolic OH
laktamelactimepurine
amphoteric
Q. 44.
caffeine
1,3,7-trimethyl-xanthine
N
N N
N
O
O
CH3
H3CCH3
1
2
3
4
7
8
9
5
6
no tautomerisation
Q. 44.
N
N N
N
O
O
CH3
H3CH
theophylline
1,3-dimethy-xanthine
1
2
3
4
7
8
9
5
6
no tautomerisation
Q. 44.
theobromine
3,7-dimethyl-xanthine
1
2
3
4
7
8
9
5
6
amphoteric
N
N N
N
O
O
CH3
HCH3
Q. 44.
adenine
Q. 44.
N
N N
N
N H 2
Hpurine
1
2
3
4
7
8
9
5
6
guanine
Q. 44.
HN N
N
O
HN
H 2N
1
2
3
4
78
9
5
6
uridine
-D-ribofuranosyl-uracil
(RNA)
HN
NO
HO CH2
H
H
OH
H
H
OH
O
O
CH3N
NO
HO CH2
H
H
OH
H
H
OH
O
O
N
NO
NH2
HO CH2
H
H
OH
H
H
OH
O
H
thymidine
-D-ribofuranosyl-thymine
(DNA)
cytidine
-D-ribofuranosyl-citosin
ribose
cytosine
C
uracil
U thymine
T12
3 45
6
1’
2’3’
4’
5’
pyrimidine
pyrimidine bases
Q. 45.
guanosine
-D-ribofuranosyl-guanine
O
OH
H
H
OH
H
H
CH2HO
NH2
N
NN
N
O
OH
H
H
OH
H
H
CH2HO
N N
N
O
HN
H2N
adenine
A
guanine
G
ribose
purine bases
adenosine
-D-ribofuranosyl-adenine
purine 1
2 34
7
8
9
56
Q. 45.
AMP
(adenosine-5’-monophosphate)
ADP
(adenosine-5’-diphosphate)
ester bond ester bondanhydride bond
phosphateribose
pyrophosphate
adenine
Q. 45.
N
N N
N
NH2
CH2
H
H
OH
H
H
OH
OOPO
O
O
POP
O
O
O
O
O
ATP
(adenosine-5’-triphosphate)
cAMP
(adenosine-3’,5’-phosphate)
O CH2
H
O
NH2
N
N N
N
H
OH
H
H
OP
O
O
triphosphate
„lacton”
5’
3’
Q. 45.
AZT
(3’-azido-2’,3’-dideoxy-thymidine)
CH2
H
O
N
H
H
H
HN
O
O
CH3
HO
HN3azido group
Q. 45.
nucleotide
nucleoside
RNA
(ribonucleic acid)
adenine
guanine
uracil
citozine
phosphate
ester
O
OH
H
H
H
H
CH2OP
O
O
O P
O
O
O CH2 O
OH
H
H
H
H
O P
O
O
O CH2
N
NN
N
NH2
N
NN
N
H2N
OH
O
OH
H
H
H
H
N
N
OH
O
O P
O
O
O CH2 O
OH
H
H
H
H
N
N
O
NH2
O
P
O
O
Q. 46.
DNA
(deoxyribonucleic acid)
OH
H
H
H
N
N
O
NH2
O
P
O
OH
O P
O
O
O CH2
OH
H
H
H
N
HN
O
O
H
CH3
N
NN
HN
H2N
O
N
NN
N
NH2
OH
H
H
H
O P
O
O
O CH2
H
OH
H
H
H
CH2OP
O
O
O P
O
O
O CH2
H
adenin
guanin
timin
citozinP P PP OH
A G T C
3’
5’
dAdGdTdC
Q. 46.
CH2
H
OH
O
H
OH
H
H
N
CONH2
O
PO OH
O
CH2
H
OH
O
NH2
N
N N
N
H
OH
H
H
O
PO OH
anhydride
bond
ester bond
nicotinic amide
adenine
NAD+
(nicotinic amide-adenine-dinucleotide)
Q. 47.
N H
CONH2
+
NH
CONH2
H
:
NAD+
2e-/H
NADH
Q. 47.
FAD
(flavine-adenine-dinucleotide)
CH2
H
OH
O
NH2
N
N N
N
H
OH
HH
OP
O
O
N
N
NH
N
O
O
CH2C
C
CH
H
H
OH
OH
OH
CH H
O
P
O
OO
H3C
H3C
dimethyl-isoalloxantine
ribitol
pyrphosphate
adenine
ribose
Q. 47.
FADH2
N
N
NH
N
O
O
R
NH
N
NH
NH
O
O
R
H2C-COO-
H2C-COO-
succinate
+
FAD
COO-H
H COO-
fumarate
+
2H/2e-
Q. 47.
CH2
SH
CH2
NH
CO
CH2
CH2
NH
CO
C
C
CH2
CH3H3C
H OH
O P
O
O
O
P
O
O
O
CH2
C C
C
O
C
HH H
H
OHO
P OO
O
NH2
N
NN
N
Co-A
(coenzim-A)
amide bond
pantotheic
acid
thioethanol amin
pyrophosphate
phosphate
ribose
adenine
anhydride bond
ester bond
Q. 47.
creatinine
N C
C
N
C
CH3
OHN
H2
H
Q. 48.
guanido gruop
creatine phosphate
CHNN
CH3
CH2 COO-
N PO32-H
Q. 48.
phosphoguanido group
barbituric acid
C
NC
CH2
CNH
O
OO
H
Q. 48.
diureide
atropine
N
H
O
CH3
CO
CHHOCH2
ester bond
tropic acid
-phenyl--hydroxy-
propionic acid
tropine
*
1 2
3
4
7
5
6
Q. 49.
cocaine
NCH3COOCH3
H
H
OCO
benzoic acidecgonine
ester bond
Q. 49.
morphine
O
H
NCH3
HO
HOphenolic OH
alcoholic OH
furane
pyperidine
Q. 49.
LSD
(lysergic acid diethylamide)
N
N
H
CO
CH3(C2H5)2N
Hindole
quinoline
lysergic acidamide bond
Q. 49.
quinine
N
CHOHN
CH2
CH2
CH CH2
CH3O
vinyl group
quinoline
quinuclidine
Q. 49.
nicotine
2-(3’)-pyridyl-N-methyl-pyrrolidine
N
NCH3pyridine
pyrrolidine
1
2
3 4
2’
3’
4’
5’
5
1’
6’
Q. 49.
coniine
(2-propyl-pyperidine)
12
3
4
5
6
N CH2CH2CH3
Hpyperidine
Q. 49.
mescaline
CH2CH2 NH2CH3O
CH3O
CH3O
pyrrogallol
ethylamin
Q. 49.
(-)-efedrin
*
*
C
C
CH3
NHCH3H
H OH
Q. 49.
ephedrine
-tokoferol
(vitamin E)
O
CH3
CH3 CH3 CH3
HO
CH3
OH
H3CCH3
benzoxane
4,8,12-trimethyl-tridecyl group
Q. 51.
vitamins K
n = 4 vitamin K1 (phylloquinone)
n = 6 vitamin K2 (menaquinone)
naphthoquinone
O
O
H
n
Q. 51.
ubiquinone
Coenzyme-Q
n = 5-10
n
CH3
O
O
CH3O
CH3O H
benzoquinone
Q. 51.
vitamin B1
tiamine
H3C N
NCH3
CH2CH2OHS
N
NH2
pyrimidine tiazol
Q. 51.
Riboflavin
vitamin B2
N
NNH
N O
O
H3C
H3C
CH2
C
C
C
CH2
H
H
H
HO
HO
HO
HO
isoalloxanthine
ribitol
Q. 51.
Pyridoxal
vitamin B6
N
OH
CH3
CHO
H2CHO
Q. 51.
pyridine ring
phenolic OHprimary alcoholic OH
aldehyde/formil group
Panthotheic acid
(,-dihydroxy-,-dimethyl-butyric acid)
HO CH2 C CH C NH CH2 CH2 COOH
CH3
OHC
O
H3 -alanine
panthionic acid
Q. 51.
Folic acid
(pteroyl-glutamic acid)
N
N
N
N
OH
H2N
CH2 NH C
O
NH CH CH2 CH2
COOH
COOH
amide bond
p-amino-benzoic acid
PABA
glutamic acid
-amino-glutaric acid2-amino-4-hydroxy-
6-hydroxymethyl-pteridine
Q. 51.
vitamin C
(L-ascorbic acid)
OC
HO OH
OHCHO
CH2OH
**
1
23
4
5
6
Q. 51.
-lacton
Aspirin
C O O H
O C C H 3
O
Q. 52.
ester bond
phenacetin
N C CH3
O
OC2H5
H
Q. 52.
amide bond
sulfanilamide
H2N SO2NH2
Q. 52.
aromatic aminaromatic sulphonic amide
cephalosporines
O C H 3C O O H
S
N
N HC
N H 2
C H
O
Q. 52.
-lactame
barbiturates
NH
NH
O
O
O
R1
R2
Q. 52.
guanido group
1
2
3
4
5
6
5-fluorouracil
N
NO
O
F
H
H
Q. 52.
1
23 4
5
6
6-mercaptopurine
N
N
N
N
H
SH
Q. 52.
1
2
3
4
7
8
9
5
6
aromatic thio group
