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2-Iodoadenosine is a chemical compound that is produced from the oxidation of uridine. It is used in the synthesis of peptides, which are important for biological processes like signal transduction and cell growth.

Off-White Crystalline Solid

An intermediate in the synthesis of isoguanosine (crotonoside or 2-hydroxyadenosine), a naturally occuring nucleoside analogue of guanosine. Isoguanosine is incorporated into mammalian but not bacterial nucleic acids, stimulates the accumulation of cyclic AMP in the brain, and is an inhibitor of IMP:pyrophosphorylase.

An intermediate in the synthesis of isoguanosine (crotonoside or 2-hydroxyadenosine), a naturally occuring nucleoside analogue of guanosine. Isoguanosine is incorporated into mammalian but not bacterial nucleic acids, stimulates the accumulation of cyclic AMP in the brain, and is an inhibitor of IMP:pyrophosphorylase.

GENERAL STEPS: To a flask containing 6.0 g (11.1 mmol) of (2R,3R,4R,5R)-2-(acetyloxymethyl)-5-(6-chloro-2-iodo-9H-purin-9-yl)tetrahydrofuran-3,4-diyldiacetate was added 100 mL of liquid NH3 at -78 °C with continuous stirring for 6 hours. Subsequently, the reaction mixture was slowly warmed to room temperature and the NH3 was evaporated overnight to give a brown oil. The product was purified by hot isopropanol crystallization to give 2-iodoadenosine (80% yield, melting point 143-145°C). Thin layer chromatographic analysis (20% MeOH/CHCl3) showed an Rf value of 0.6. 1H NMR (300 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.68 (s, 2H), 5.75 (d, J = 6.16 Hz, 1H), 5.42 (d, J = 5.40 Hz, 1H), 5.16 (d, J = 4.62 Hz , 1H), 4.99 (t, J = 5.39 Hz, 1H), 4.67 (d, J = 4.81 Hz, 1H), 4.06 (d, J = 3.37 Hz, 1H), 3.89 (m, 1H), 3.54 (m, 2H).

[1] Journal of Organic Chemistry, 1985, vol. 50, # 3, p. 406 - 408
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 4, p. 1766 - 1769
[3] Journal of Organic Chemistry, 1988, vol. 53, # 13, p. 3051 - 3057
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 241 - 252
[5] Patent: US4956345, 1990, A