Description

2-Iodoadenosine (CAS No. 35109-88-7) is a modified nucleoside analog featuring an iodine substitution at the 2-position of the adenine base. With the molecular formula C₁₀H₁₂IN₅O₄ and IUPAC name (2R,3R,4S,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, this compound is a valuable biochemical tool for research applications. It is commonly used in nucleoside chemistry, enzyme studies, and as a precursor for further derivatization. The iodine moiety enhances its reactivity, making it suitable for cross-coupling reactions and radiolabeling. This high-purity compound is supplied as a crystalline solid with >95% purity (HPLC), ensuring reliability for sensitive experimental workflows. Store at -20°C under inert conditions to maintain stability.

Properties

• CAS Number: 35109-88-7
• Complexity: 367
• IUPAC Name: (2R,3R,4S,5R)-2-(6-amino-2-iodo-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• InChI: 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
• InChI Key: MGEBVSZZNFOIRB-UUOKFMHZSA-N
• Exact Mass: 392.99340
• Molecular Formula: C10H12IN5O4
• Molecular Weight: 393.14
• SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)I)N
• Topological: 140
• Monoisotopic Mass: 392.99340
• Synonyms: 2-Iodoadenosine, 35109-88-7, Adenosine, 2-iodo-, DTXSID70188607, DTXCID90111098, 2-Iodo Adenosine, (2R,3R,4S,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, (2R,3R,4S,5R)-2-(6-amino-2-iodo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol, MFCD01320413, C10H12IN5O4, 2-Iodo-guanosine, 6-Amino-2-iodo-9-(beta-D-ribofuranosyl)purine, 2-Iodoadenosine, 97%, SCHEMBL259445, CHEMBL2113519, AKOS015853969, AKOS015919384, NI04749, AC-13964, BP-58632, DA-60142, DS-18553, I0759, F12897, EN300-7403082, 6-Amino-2-iodo-9-(?-D-ribofuranosyl)purine;2-Iodo-D-adenosine, (2R,3R,4S,5R)-2-(6-amino-2-iodo-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, (4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxy-methyl)oxolane-3,4-diol, (4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Application

2-Iodoadenosine is widely utilized in biochemical research as a precursor for synthesizing modified nucleosides and nucleotides. It serves as a key intermediate in the study of adenosine receptor interactions and enzyme mechanisms, particularly in purine metabolism pathways. Researchers also employ it in radiolabeling and cross-coupling reactions for probe development. Its iodine substitution enables versatile applications in medicinal chemistry and drug discovery.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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