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2-IODOADENOSINE

Product Name2-IODOADENOSINE
CAS35109-88-7
MFC10H12IN5O4
MW393.14
EINECS623-798-8
MOL File35109-88-7.mol

Chemical Properties

Melting point	200 °C (dec.)
Boiling point	776.3±70.0 °C(Predicted)
Density	2.69±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	DMSO, Methanol, Water
form	Solid
pka	13.05±0.70(Predicted)
color	Off-White to Pale Yellow
λmax	265nm(H2O)(lit.)
InChI	1S/C10H12IN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
InChIKey	MGEBVSZZNFOIRB-UUOKFMHZSA-N
SMILES	Nc1nc(I)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
CAS DataBase Reference	35109-88-7(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26
WGK Germany	3
HS Code	29349990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Uses

2-Iodoadenosine is an intermediate in the synthesis of isoguanosine (crotonin or 2-hydroxyadenosine), a natural nucleoside analog of guanosine. Isoguanosine is incorporated into the nucleic acids of mammals, rather than bacteria, stimulating the accumulation of cyclic adenosine (AMP) in the brain, and is an inhibitor of pyrophosphorylase IMP.

Description

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.

Chemical Properties

Off-White Crystalline Solid

Synthesis

ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(6-CHLORO-2-IODO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER

5987-76-8

35109-88-7

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).

References

[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

2-IODOADENOSINE

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Usage And Synthesis

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