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Nucleotide Biosynthesis. PRPP synthesis Purines Carbamoyl phosphate synthetase II Pyrimidines Nucleoside kinases Deoxyribonucleotides. Biosynthesis of Purine Nucleotides. O. NH 2. H. N. O. N. N. N. OPO 3 CH 2. OPO 3 CH 2. O. O. N. N. HO. HO. OH. OH. 5’-UMP. 5’-AMP.

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Nucleotide biosynthesis
Nucleotide Biosynthesis

  • PRPP synthesis

  • Purines

  • Carbamoyl phosphate synthetase II

  • Pyrimidines

  • Nucleoside kinases

  • Deoxyribonucleotides


Nucleotide biosynthesis

Biosynthesis of Purine Nucleotides

O

NH2

H

N

O

N

N

N

OPO3CH2

OPO3CH2

O

O

N

N

HO

HO

OH

OH

5’-UMP

5’-AMP

Pyrimidine

Purine


Nucleotide biosynthesis

9. Add formyl-THF

2. Displace pyrophosphate with glutamine (N)

8. Get NH2 from aspartate (N)

3. Add glycine (N)

4. Add formyl-THF

6. Add glutamine (N)

C

N

C

N

C

C

7. Add CO2

C

N

N

Ribose-5-PO4

Purine Synthesis

10 Steps:

1. Activate the Ribose (PRPP)

10. Close large ring

5. Close small ring


Nucleotide biosynthesis

CH2OPO3=

CH2OPO3=

Alpha position

O

O

OPP

OH

HO

HO

OH

OH

ATP

+ AMP

PRPP

Synthetase

Ribose-5-P

5-Phosphoribosyl-PP

(PRPP)

Activate Ribose

PRPP allows ribose to be joined to a base


Nucleotide biosynthesis

CH2OPO3=

CH2OPO3=

CH2OPO3=

O

O

O

NH3

NH3

OPP

HO

HO

HO

OH

OH

OH

COO-

H3N-C-H

CH2

NH2

2C

H

CH2

H2N

C

O

=C

R

O

COO-

O

NH

H

C

NH3

H

HO

OH

5-phosphoribosylamine

5-PRPP

L-glutamine

Glycine


Nucleotide biosynthesis

NH2

2C

H

NH

NH

O

=C

2C

2C

H

H

NH

HN

2C

R

H

C

C

H

H

O

=C

=C

O

NH

C

H

C

R

R

O

O

H2N

O

O

NH

NH

R

O

NH

HO

OH

HO

HO

OH

OH

HO

OH

Formyl-THF

Glutamine

Ring

Closure


Nucleotide biosynthesis

O

O

C

NH

O

C

NH

C

H2N

C

C

H

C

H2N

C

H

C

H2N

NH

NH

R

R

COO

+

H3N-C-H

CH2

COO-

CO2

ATP

L-aspartate

+ ATP


Nucleotide biosynthesis

O

O

O

N

C

C

NH

NH

H2N

H2N

C

C

C

C

H

H

HC

C

C

H2N

N

O

NH

NH

R

R

N

C

C

C

C

H

H

C

N

O

N

Hypoxanthine

HO

OH

Formyl-THF

R= OPO3CH2

Ring closure

R

Inosine 5’-phosphate


Summary of purine biosynthesis
Summary of Purine Biosynthesis

Amino acids

Glutamine 2

Glycine 1

Aspartate 1

Coenzymes

1 PRPP synthesis

N10-formyl THF 2

1 Glutamine

Energy

1 Glycine

ATP 6

1 Aspartate

Others

1 CO2

CO2 1

1 Small ring closure

Ribose-5-PO4 1


Nucleotide biosynthesis

-COO-CH2-CH-COO-

O

NH2

NH

N

N

N

H

H

C

N

H

C

N

R

R

O

N

N

N

N

N

R

O

C

C

C

C

C

C

C

C

C

C

N

C

C

C

C

C

H

N

C

H

C

C

C

C

C

H

H

H

H

H

N

H

C

C

O

N

N

R

H2

N

O

O

O

O

O

R

N

N

N

N

N

HO

HO

HO

HO

HO

OH

OH

OH

OH

OH

Asp + GTP

5’AMP

NAD+

Adenylsuccinate

Glutamine

5’-XMP

ATP

5’-GMP


Nucleotide biosynthesis

5’-AMP

ADP

ATP

5’-IMP

dADP

dATP

5’-XMP

5’-GMP

GDP

GTP

Summary of Purine

Nucleotide Biosynthesis

dGDP

dGTP