Department of Biochemistry, KMC, Duwakot, Nepal
Thursday, February
4, 2016
Rajesh Chaudhary
1
Thursday, February
4, 2016
Rajesh Chaudhary
2
Why do we need to study nucleotides?
Principal acceptor and donor of phosphoryl group in
cellular metabolism.
Energy currency in metabolic transition.
Structural components of enzyme cofactors in Vitamins.
Constitutes of nucleic acids (DNA & RNA).
Thursday, February
4, 2016
Rajesh Chaudhary
3
Synthetic nucleotide analogs are used in
chemotherapy
Used in treatment of
hyperuricemia and gout by
inhibiting purine biosynthesis and
xanthine oxidase activity. Used in chemotherapy of Cancer
Thursday, February
4, 2016
Rajesh Chaudhary
4
Why do we need to study nucleotides?
Nucleotide serves as diverse physiologic
functions
Rajesh Chaudhary
5
Figure A.
Figure B.
Figure C.
cAMP cGMP
S-adenosylmethionine
When the phosphate group is absent,
the compound is known as a
nucleoside.
Nucleotides
Characteristics components
Thursday, February
4, 2016
Rajesh Chaudhary
6
Purine and Pyrimidine
Are heterocyclic compounds.
Nucleosides are N-Glycosides.
Nucleotides are phosphorylated nucleosides.
Heterocyclic N-Glycosides exist as Syn and Anti
conformers.
Thursday, February
4, 2016
Rajesh Chaudhary
7
Syn and Anti conformers
Thursday, February
4, 2016
Rajesh Chaudhary
8
Ribonucleosides drawn as Syn conformers
Thursday, February
4, 2016
Rajesh Chaudhary
9
The C1 of the pentose attached with N1 of the PYRIMIDINE and N9 of Purine.
Nucleotides are Phosphorylated Nucleosides
Thursday, February
4, 2016
10
Purine or
Pyrimidine
X = H X = Ribose X = Ribose
phosphate
Adenine Adenosine Adenosine
monophosphate
(AMP)
Guanine Guanosine Guanosine
monophosphate
(GMP)
Cytosine Cytidine Cytidine
monophosphate
(CMP)
Uracil Uridine Uridine
monophosphate
(UMP)
Thymine Thymidine Thymidine
monophosphate
(TMP)
Rajesh Chaudhary
11
Thursday, February
4, 2016
Rajesh Chaudhary
12
Thursday, February
4, 2016
Rajesh Chaudhary
13
How pentose sugar is different between ribose and deoxyribose?
Key convention
Although DNA and RNA have two distinctions –
different pentose and presence of Uracil in RNA and
Thymine in DNA – it is the pentose that defines the
identity of a nucleic acid.
Thursday, February
4, 2016
Rajesh Chaudhary
14
— Lehninger’s Principles of Biochemistry
Modification of polynucleotides can generate additional
structures.
Nucleotides are polyfunctional acids.
Nucleotides absorb ultraviolet light.
Nucleotides serve diverse physiologic functions.
Nucleoside triphosphate have high-group transfer potential.
Thursday, February
4, 2016
Rajesh Chaudhary
15
Thursday, February
4, 2016
Rajesh Chaudhary
16
Synthetic nucleotide analogs are used in chemotherapy.
Nonhydrolyzable Nucleoside Triphosphate analogs serve as
research tools.
DNA and RNA are polynucleotides
Polynucleotides are directional macromolecules
Polynucleotide are directional molecules
Thursday, February
4, 2016
Rajesh Chaudhary
17
Phosphodiester bonds link the 3’ 5’-carbons of adjacent monomers.
Primary structure
More compact notification
Modification of Polynucleotides can generate
additional structures
Thursday, February
4, 2016
18
Bacterial and Human
DNA
Bacterial and
Viral nucleic acid
… of mammalian mRNA
that function in
oligonucleotide recognition
and in regulation of half-
lives of RNAs.
Thursday, February
4, 2016
Rajesh Chaudhary
19

Nucleotides

  • 1.
    Department of Biochemistry,KMC, Duwakot, Nepal Thursday, February 4, 2016 Rajesh Chaudhary 1
  • 2.
  • 3.
    Why do weneed to study nucleotides? Principal acceptor and donor of phosphoryl group in cellular metabolism. Energy currency in metabolic transition. Structural components of enzyme cofactors in Vitamins. Constitutes of nucleic acids (DNA & RNA). Thursday, February 4, 2016 Rajesh Chaudhary 3
  • 4.
    Synthetic nucleotide analogsare used in chemotherapy Used in treatment of hyperuricemia and gout by inhibiting purine biosynthesis and xanthine oxidase activity. Used in chemotherapy of Cancer Thursday, February 4, 2016 Rajesh Chaudhary 4 Why do we need to study nucleotides?
  • 5.
    Nucleotide serves asdiverse physiologic functions Rajesh Chaudhary 5 Figure A. Figure B. Figure C. cAMP cGMP S-adenosylmethionine
  • 6.
    When the phosphategroup is absent, the compound is known as a nucleoside. Nucleotides Characteristics components Thursday, February 4, 2016 Rajesh Chaudhary 6
  • 7.
    Purine and Pyrimidine Areheterocyclic compounds. Nucleosides are N-Glycosides. Nucleotides are phosphorylated nucleosides. Heterocyclic N-Glycosides exist as Syn and Anti conformers. Thursday, February 4, 2016 Rajesh Chaudhary 7
  • 8.
    Syn and Anticonformers Thursday, February 4, 2016 Rajesh Chaudhary 8
  • 9.
    Ribonucleosides drawn asSyn conformers Thursday, February 4, 2016 Rajesh Chaudhary 9 The C1 of the pentose attached with N1 of the PYRIMIDINE and N9 of Purine.
  • 10.
    Nucleotides are PhosphorylatedNucleosides Thursday, February 4, 2016 10
  • 11.
    Purine or Pyrimidine X =H X = Ribose X = Ribose phosphate Adenine Adenosine Adenosine monophosphate (AMP) Guanine Guanosine Guanosine monophosphate (GMP) Cytosine Cytidine Cytidine monophosphate (CMP) Uracil Uridine Uridine monophosphate (UMP) Thymine Thymidine Thymidine monophosphate (TMP) Rajesh Chaudhary 11
  • 12.
  • 13.
    Thursday, February 4, 2016 RajeshChaudhary 13 How pentose sugar is different between ribose and deoxyribose?
  • 14.
    Key convention Although DNAand RNA have two distinctions – different pentose and presence of Uracil in RNA and Thymine in DNA – it is the pentose that defines the identity of a nucleic acid. Thursday, February 4, 2016 Rajesh Chaudhary 14 — Lehninger’s Principles of Biochemistry
  • 15.
    Modification of polynucleotidescan generate additional structures. Nucleotides are polyfunctional acids. Nucleotides absorb ultraviolet light. Nucleotides serve diverse physiologic functions. Nucleoside triphosphate have high-group transfer potential. Thursday, February 4, 2016 Rajesh Chaudhary 15
  • 16.
    Thursday, February 4, 2016 RajeshChaudhary 16 Synthetic nucleotide analogs are used in chemotherapy. Nonhydrolyzable Nucleoside Triphosphate analogs serve as research tools. DNA and RNA are polynucleotides Polynucleotides are directional macromolecules
  • 17.
    Polynucleotide are directionalmolecules Thursday, February 4, 2016 Rajesh Chaudhary 17 Phosphodiester bonds link the 3’ 5’-carbons of adjacent monomers. Primary structure More compact notification
  • 18.
    Modification of Polynucleotidescan generate additional structures Thursday, February 4, 2016 18 Bacterial and Human DNA Bacterial and Viral nucleic acid … of mammalian mRNA that function in oligonucleotide recognition and in regulation of half- lives of RNAs.
  • 19.