2-IODOADENOSINE 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.)

InChIKey

MGEBVSZZNFOIRB-UUOKFMHZSA-N

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

2-IODOADENOSINE 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

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(35109-88-7)Related Product Information

• Vidarabine
• 2-Fluoroadenosine
• Adenosine 5'-monophosphate
• PROMETHAZINE
• Aminophylline
• S-ADENOSYL-L-METHIONINE
• Doxofylline
• Adenosine
• Cyclic adenosine monophosphate
• 2-Iodopyrimidine
• 2-Iodoadenine
• 2-IODOADENOSINE
• 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE
• 2-IODOADENOSINE 2',3'-ACETONIDE
• 2-Azido-6-iodoadenosine
• 2-IODOADENOSINE 5'-CARBOXY-2',3'-ACETONIDE
• TFA & 2-IODOADENOSINE
• 2'-deoxy-2'-iodoadenosine-5'-triphosphate