nucleotides

Department of Biochemistry, KMC, Duwakot, Nepal

Thursday, February

4, 2016Rajesh Chaudhary

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Thursday, February


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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


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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 CancerThursday, February


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Why do we need to study nucleotides?

Nucleotide serves as diverse physiologic

functions

Rajesh Chaudhary

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Figure A.

Figure B.

Figure C.

cAMP cGMP

S-adenosylmethionine

When the phosphate group is absent,

the compound is known as a

nucleoside.

NucleotidesCharacteristics components

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Purine and Pyrimidine

Are heterocyclic compounds.

Nucleosides are N-Glycosides.

Nucleotides are phosphorylated nucleosides.

Heterocyclic N-Glycosides exist as Syn and Anti

conformers.

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Syn and Anti conformers

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Ribonucleosides drawn as Syn conformers

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The C1 of the pentose attached with N1 of the PYRIMIDINE and N9 of Purine.

Nucleotides are Phosphorylated Nucleosides

Thursday, February

4, 2016

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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

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How pentose sugar is different between ribose and deoxyribose?

Key conventionAlthough 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.

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— 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.

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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

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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

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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.

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nucleotides

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