Structure of purine and pyrimidine nucleotides Vladimíra Kvasnicová.

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Presentation transcript:

Structure of purine and pyrimidine nucleotides Vladimíra Kvasnicová

nucleotide = ester of phosphoric acid and a nucleoside nucleoside = N-containing base + monosaccharide  -N-glycosidic bond between base and saccharide nucleotide bases: aromatic heterocycles  purines: pyrimidine + imidazole ring  pyrimidines: pyrimidine ring

Classification of nucleotides purine nucleotides: contain adenine, guanine, (and hypoxanhine and xanthine = metabolic intermediates) pyrimidine nucleotides: contain cytosine, uracil or thymine ribonucleotides (saccharide: ribose) deoxyribonucleotides (saccharide: deoxyribose)  formed by reduction of ribonucleosides

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley ‑ Liss, Inc., New York, ISBN 0 ‑ 471 ‑ ‑ 2 PURINE BASES

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley ‑ Liss, Inc., New York, ISBN 0 ‑ 471 ‑ ‑ 2 ribonucleoside deoxyribonucleoside N-glycosidic bond

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley ‑ Liss, Inc., New York, ISBN 0 ‑ 471 ‑ ‑ 2 ribonucleotide deoxyribonucleotide

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley ‑ Liss, Inc., New York, ISBN 0 ‑ 471 ‑ ‑ 2 PYRIMIDINE BASES

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley ‑ Liss, Inc., New York, ISBN 0 ‑ 471 ‑ ‑ 2 ribonucleosides deoxyribonucleoside (RNA) (DNA)

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley ‑ Liss, Inc., New York, ISBN 0 ‑ 471 ‑ ‑ 2 Ribonucleotides * N-glycosidic bond * ester bond * anhydride bond (energy rich bond)

Properties of nucleotides strong absorption of UV radiation (260 nm) purines are less stable under acidic conditions than pyrimidines polar terminal phosphate groups  alternative names: e.g. adenosine triphosphate (ATP) = adenylate or adenylic acid