4099-81-4

Basic information

• Product Name: 5'-IODO-5'-DEOXYADENOSINE
• Synonyms: 5'-DEOXY-5'-IODO-ADENOSINE;5'-IODO-5'-DEOXYADENOSINE;5'-Deoxy-5'-iodo-D-adenosine;5''-IODO-5''-DEOXYADENOSINE 95%;5''-DEOXY-5''-JOD-ADENOSINE;5'-Iodo-5'-deoxyadenosine,95%;5'-Iodo-5'-deoxyadenosine,99+%;5'-Iodoadenosine
• CAS NO: 4099-81-4
• Molecular Formula: C₁₀H₁₂IN₅O₃
• Molecular Weight: 377.14
• EINECS: 223-864-2
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 4099-81-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 178-187 °C
• Boiling Point: 671.1°Cat760mmHg
• Flash Point: 359.7°C
• Appearance: /
• Density: 1.7865 (estimate)
• Storage Temp.: -20°C
• CAS DataBase Reference: 5'-IODO-5'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-IODO-5'-DEOXYADENOSINE(4099-81-4)
• EPA Substance Registry System: 5'-IODO-5'-DEOXYADENOSINE(4099-81-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 4099-81-4(Hazardous Substances Data)

Usage

Description

5'-IODO-5'-DEOXYADENOSINE, also known as Idoxuridine, is an antiviral medication that belongs to the class of nucleoside analogs. It is an iodinated derivative of the nucleoside adenosine, which is a fundamental component of DNA and RNA. 5'-IODO-5'-DEOXYADENOSINE is characterized by its off-white to beige crystalline powder appearance and is widely recognized for its antiviral properties.

Uses

Used in Pharmaceutical Industry:
5'-IODO-5'-DEOXYADENOSINE is used as an antiviral agent for the treatment of viral infections, particularly ocular herpes simplex infections. It works by inhibiting viral DNA synthesis and is effective in reducing the severity and duration of the infection.
Used in Research and Development:
In the field of research, 5'-IODO-5'-DEOXYADENOSINE is used as an important precursor for the synthesis of nucleotides, sugar nucleosides, and other biologically active substances. Its unique structure allows scientists to explore its potential applications in the development of new antiviral drugs and therapies.
Used in Drug Synthesis:
5'-IODO-5'-DEOXYADENOSINE is also used as a key intermediate in the synthesis of various pharmaceutical compounds, including other antiviral medications and cancer treatments. Its role as a precursor enables the development of novel drugs with improved efficacy and reduced side effects.

Upstream product

• 30685-66-6 5'-iodo-5'-deoxy-2',3'-O-isopropylideneadenosine 
• 58-61-7 adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 

Downstream Products

• 20535-04-0 9-(Desoxy-5 β-D-erythro-pent-4-enofuranosyl)adenine 
• 4754-39-6 5'-deoxyadenosine 
• 68200-73-7 6-N-benzoyl-9-(5-deoxy-β-D-erythro-pent-4-enofuranosyl)adenine 

Relevant articles and documents

Characterization and Mechanistic Study of the Radical SAM Enzyme ArsS Involved in Arsenosugar Biosynthesis

Arsenosugars are a group of arsenic-containing ribosides that are found predominantly in marine algae but also in terrestrial organisms. It has been proposed that arsenosugar biosynthesis involves a key intermediate 5′-deoxy-5′-dimethylarsinoyl-adenosine (DDMAA), but how DDMAA is produced remains elusive. Now, we report characterization of ArsS as a DDMAA synthase, which catalyzes a radical S-adenosylmethionine (SAM)-mediated alkylation (adenosylation) of dimethylarsenite (DMAsIII) to produce DDMAA. This radical-mediated reaction is redox neutral, and multiple turnover can be achieved without external reductant. Phylogenomic and biochemical analyses revealed that DDMAA synthases are widespread in distinct bacterial phyla with similar catalytic efficiencies; these enzymes likely originated from cyanobacteria. This study reveals a key step in arsenosugar biosynthesis and also a new paradigm in radical SAM chemistry, highlighting the catalytic diversity of this superfamily of enzymes.

Nicotinamide-Containing Di- and Trinucleotides as Chemical Tools for Studies of NAD-Capped RNAs

We report the chemical synthesis of a set of nicotinamide adenine dinucleotide (NAD) cap analogues containing chemical modifications that reduce their susceptibility to NAD-RNA-degrading enzymes. These analogues can be incorporated into transcripts in a similar way as NAD. Biochemical characterization of RNAs carrying these caps with DXO, NudC, and Nudt12 enzymes led to the identification of compounds that can be instrumental in unraveling so far unaddressed biological aspects of NAD-RNAs.

Large-scale, protection-free synthesis of Se-adenosyl-l-selenomethionine analogues and their application as cofactor surrogates of methyltransferases

S-Adenosyl-l-methionine (SAM) analogues have previously demonstrated their utility as chemical reporters of methyltransferases. Here we describe the facile, large-scale synthesis of Se-alkyl Se-adenosyl-l-selenomethionine (SeAM) analogues and their precursor, Se-adenosyl-l-selenohomocysteine (SeAH). Comparison of SeAM analogues with their equivalent SAM analogues suggests that sulfonium-to-selenonium substitution can enhance their compatibility with certain protein methyltransferases, favoring otherwise less reactive SAM analogues. Ready access to SeAH therefore enables further application of SeAM analogues as chemical reporters of diverse methyltransferases.