LESSON 3. - ncsa.runcsa.ru/upload/student/doc_raspisanie_2020-04-06_21-29-21.pdf · a. Both of the...
Transcript of LESSON 3. - ncsa.runcsa.ru/upload/student/doc_raspisanie_2020-04-06_21-29-21.pdf · a. Both of the...
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LESSON № 3.
The biosynthesis and breakdown of purine and pyrimidinebases. Quantitative determination of uric acid in the blood
serum.
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Nucleotides are the monomeric units of the nucleic acids: DNA and RNA. Each nucleotide contains a heterocyclic nitrogenous base (purine or pyrimidine), sugar (ribose or deoxyribose, and phosphate. Both DNA and RNA contain the same purine bases: adenine (A) and guanine (G). Both DNA and RNA contain the pyrimidine cytosine (C), but they differ in the second pyrimidine base; DNA contains thymine (T) whereas RNA contains uracil (U). The addition of a pentose sugar to a base by N-glycoside linkages produces a nucleoside. The ribonucleosides of A, G, C, T and U are named adenosine, guanosine, cytidine, thymidine, and uridine respectively. If the sugar is ribose, a ribonucleoside is produced; if the sugar is 2- deoxyribose a deoxyribonucleoside is produced. When the phosphate group is attached by an ester linkage to the 5'-OH of the pentose such a compound is called a nucleoside 5'-phosphate or a 5'-nucleotide.
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Remember: The purine ring is built on a molecule of PRPP. There are severalsources of ribose-5 phosphate.a. Glucose metabolism.b. Nucleoside degradation generates ribose-1- phosphate, which can be
converted to ribose-5 phosphate.PRPP is required in:a. The de novo synthesis of purine and pyrimidine nucleotides.
b. The salvage pathways for purine nucleotides.c. The biosynthesis of nucleotide coenzymes.Note: De novo synthesis of purine nucleotides is regulated by feedback inhibition
.a. Both of the enzymes that catalyze the first two steps of IMP synthesis – PRPP
synthetase and PRPP amidotransferase –are inhibited by IMP, GMP and AMP.b. PRPP amidotransferase has two allosteric sites: one for IMP and GMP, and one
for AMP. If both sites are occupied, then inhibition is synergistic.c. Inhibition. The synthesis of adenylosuccinate from IMP is inhibited by AMP,
and the synthesis of XMP is inhibited by GMP.
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+ + ГТФ
инозиновая кислота
аспарагиновая кислота
OCH2
H
H
OH
H
OH
H
O
OH
O
OH
P
N
NNH
N
O
COOHCHNH2
COOH
CH2
+ Ф + ГДФ
адениля нтарная кислота
OCH2
H
H
OH
H
OH
H
O
OH
O
OH
P
N
NN
N
NH
CHCH2
COOH COOH
H H
OCH2
H
OH OH
H
O
OH
O
OH
P
N
NN
N
NH2
+ Ф + ГДФ+
CH
CH
COOH
COOH
адениловая кислота
фумаровая кислота
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инозиновая кислота
+ 1/2
ксантиловая кислота
OCH2
H
H
OH
H
OH
H
O
OH
O
OH
P
N
NNH
N
O
O2
OCH2
H
H
OH
H
OH
H
O
OH
O
OH
P
N
NNH
NH
O
O
ксантиловая кислота
+
глутамин
+ АТФCOOHCHNH
2
CH2
CH2
CO NH2
OCH2
H
H
OH
H
OH
H
O
OH
O
OH
P
N
NNH
NH
O
O
гуаниловая кислота
+ АМФ + ФФ
глутаминовая кислота
+OCH
2
H
H
OH
H
OH
H
O
OH
O
OH
P
N
NNH
N
O
NH2
COOHCHNH2
CH2
CH2
COOH
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+ АТФкарбаматкиназа
+ + АДФNH3
CO2 O P O
OH
OH
CONH2
O P O
OH
OH
CONH2
карбамилфосфат
+
NH2
CH COOH
CH2
COOH
аспарагиновая кислота
аспартаткарбамилтрансфераза
CONH2
NH CH COOH
CH2
COOH
карбамил-аспарагиновая кислота
+ Ф
COOH
CH2
H2N CO NH CH COOH
дигидрооротаза
-Н2О
CH2
NH
NH
О
ОСООН
дигидрооротовая кислота
_ _ _ _
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дигидрооротовая кислота
дигидрооротатдегидрогеназа + ФАД
- ФАД.Н2
оротовая кислота
NH
C CH
CH2
O
C
O
COOHNH
NH
C C
CH
O
C
O
COOHNH
оротовая
кислота
+
5'-фосфорибозил-1'-пирофосфат
оротидин-5'-фосфатпиро-
фосфарилаза
оротидин-5'-фосфат
+
пирофосфат
NH
C C
CH
O
C
O
COOHNH
O P
OH
OH
O CH2
H
O
OH
H H
OH
H
NH
NO
O
COOH
O P
OH
OH
O CH2
H
O
OH
H H
OH
H
OP
O
OH
O P
O
OH
OH
OP
O
OH
P
O
OH
OHOH
оротидин-5'-фосфат
оротидин-5'-фосфатдекар- боксилаза
-
уридин-5'-монофосфат
CO2
O P
OH
OH
O CH2
H
O
OH
H H
OH
H
NH
NO
O
COOH
O P
OH
OH
O CH2
H
O
OH
H H
OH
H
NH
NO
O
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аденозин-3'-фосфат
3'-нуклеотидаза
+ H2O +
аденозин
O
H
O
H
OH
HH
N
NN
N
CH2
OH
P
O
OHOH
NH2
O
H H
OH
HH
N
NN
N
CH2
OH
NH2
OH
OH
P O
OH
OH
O
H H
OH
HH
N
NN
N
CH2
OH
NH2
OH
OH
P O
OH
OH+
аденозин
аденозинфосфорилаза
OH P
O
OH
OO
H H
OH
HH
CH2
OH
OH
NH
NN
N
NH2
рибозо-1-фосфат
+
аденин
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N
NN
N
NH2
O
H H
OHOH
HH
CH2
OH
аденозин
нуклеозидаза + H
2O
O
H H
OHOH
HH
CH2
OH OH
рибоза
+
аденин
NH
NN
N
NH2
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аденин
NH
NN
N
NH2
аденинаминогидролаза +
гуанинаминогидролаза +
H2O
H2O
NH3
NH3
+
NH
N
N
OH
N
NH
NNH
N
O
гипоксантин(енольная форма)
гипоксантин (кетоформа)
NH
NN
N
OH
NH2
гуанин
+
NH
NN
N
OH
OH NH
N
O
O
NH
NH
ксантин(енольная форма)
ксантин (кетоформа)
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N
N
NH2
OH
цитозин
цитозинаминогидролаза + H
2O
NH3 +
N
NOH
OH
NH
NHO
O
урацил(енольная форма)
+
урацил (кетоформа)
NH
NNH
N
O
гипоксантин
ксантиноксидаза + 1/2
ксантиноксидаза + 1/2 O
2O
2
NH
NNH
NH
O
O
ксантинNH
NH
NH
O
O O
NH
мочевая кислота
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урикооксидаза (уриказа)+ 1/2 +
-
мочевая кислота аллантоин
аллантоиназа +
аллантоиновая кислота
+2 +
мочевина глиоксиловая кислота
NH
NHNH
O O
O
O2 H
2O
CO2
NH
NHNH2
O O
O
H2O
NH
NH2
CNH2
O O
O OHH
2O
C O
NH2
NH2
C
C
OHO
H O
NHNH
NH
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NH
O
NHO
урацил
дигидроурацилдегидрогеназа + НАД.Н2
- НАД
NH
O
NHO
дигидроурацил
дигидропиримидиназа + H
2O
NH2
C CH2
CH2
C
O
NHO
OH
N-карбамил-бета-аланин
N-карбамил-бета-аланин- амидогидролаза
H2O+
бета-аланин
COOH
CH2
CH2
NH2
NH2
COOH
NH3 CO
2
карбаминовая кислота
+
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