611-53-0

Basic information

• Product Name: 5-Iodo-2'-deoxycytidine
• Synonyms: 5-Iodo-deoxycytidine;4-aMino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)oxolan-2-yl]-5-iodo-1,2-dihydropyriMidin-2-one;4-AMino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-iodopyriMidin-2(1H)-one;5-Iodo-2′-deoxycytidine, >=99%;IDC;IBACITABINE;5-IDC;5-IODO-2'-DEOXYCYTIDINE
• CAS NO: 611-53-0
• Molecular Formula: C₉H₁₂IN₃O₄
• Molecular Weight: 353.11
• EINECS: 210-269-8
• Product Categories: Amino Acids;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 611-53-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 180-183℃
• Boiling Point: 522.1 °C at 760 mmHg
• Flash Point: 269.6 °C
• Appearance: White/Powder
• Density: 2.37 g/cm³
• Storage Temp.: Store at 0°C
• PKA: 14.03±0.60(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 5-Iodo-2'-deoxycytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodo-2'-deoxycytidine(611-53-0)
• EPA Substance Registry System: 5-Iodo-2'-deoxycytidine(611-53-0)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-63-42/43-36/37/38
• Safety Statements: 23-26-36/37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 611-53-0(Hazardous Substances Data)

Usage

Description

5-Iodo-2'-deoxycytidine is an iodinated analog of deoxycytidine and acts as an anti-viral agent.

Chemical Properties

White crystals or powder

Uses

5-Iodo-2'-deoxycytidine is used in the construction of DNA oligomers to enable structural studies and photoactivated cross-linking. It is used in the synthesis of other modified nucleosides, such as 5-ethynylferrocenyl-2?-deoxycytidine used in semiconductor electrodes and 10-(2-deoxyβ-D-ribofuranosyl)pyrimido[4?,5?:4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dCPPI).

Upstream product

• 951-77-9 2'-Deoxycytidine 
• 3992-42-5 2'-deoxycytidine monohydrochloride 
• 207121-53-7 2'-deoxycytidine monohydrate 

Downstream Products

• 647852-34-4 5-(4-benzoylthio-1-butynyl)-2'-deoxycytidine 
• 192124-98-4 N⁴-benzoyl-O^5'-(4'',4'''-dimethoxytriphenylmethyl)-5-{2-[3-(2,2,5,5-tetramethyl-3-pyrrolin-1-yloxy)]ethynyl}-2'-deoxycytidine 
• 192124-97-3 N⁴-benzoyl-5-{2-[3-(2,2,5,5-tetramethyl-3-pyrrolin-1-yloxy)]ethynyl}-2'-deoxycytidine 
• 375346-79-5 N-{1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-prop-1-ynyl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 515850-82-5 N⁴,N⁴-dibenzoyl-1-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]-5-iodocytosine 
• 515850-83-6 N⁵-benzoyl-2-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]pyrimido[4,5-c]isoquinoline-3,6-dione 
• 669776-74-3 3'-O,4-N-diacetyl-5'-O-4,4'-dimethoxytrityl-5-(3''-trifluoroacetamidobutynyl)-2'-deoxycytidine 
• 669776-76-5 3'-O-acetyl-5'-O-4,4'-dimethoxytrityl-5-(3''-trifluoroacetamidobutynyl)-2'-deoxycytidine 
• 669776-73-2 4-[3'-O,4-N-diacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidin-5-yl]but-3-ynyl tert-butyl disulfide 
• 669776-72-1 5'-O-4,4'-dimethoxytrityl-5-(3''-trifluoroacetamidobutynyl)-2'-deoxycytidine 
• 669776-75-4 4-[3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidin-5-yl]but-3-ynyl tert-butyl disulfide 
• 669776-71-0 5'-O-4,4'-dimethoxytrityl-5-(4-benzoylthio-1-butynyl)-2'-deoxycytidine 
• 647852-37-7 4-[5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidin-5-yl]but-3-ynyl tert-butyl disulfide 
• 717876-96-5 4-N-(N,N-dimethylaminomethylidenyl)-5-iodo-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine 

Relevant articles and documents

Fluorogenic Labeling of 5-Formylpyrimidine Nucleotides in DNA and RNA

5-Formylcytosine (5fC) and 5-formyluracil (5fU) are natural nucleobase modifications that are generated by oxidative modification of 5-methylcytosine and thymine (or 5-methyluracil). Herein, we describe chemoselective labeling of 5-formylpyrimidine nucleotides in DNA and RNA by fluorogenic aldol-type condensation reactions with 2,3,3-trimethylindole derivatives. Mild and specific reaction conditions were developed for 5fU and 5fC to produce hemicyanine-like chromophores with distinct photophysical properties. Residue-specific detection was established by fluorescence readout as well as primer-extension assays. The reactions were optimized on DNA oligonucleotides and were equally suitable for the modification of 5fU- and 5fC-modified RNA. This direct labeling approach of 5-formylpyrimidines is expected to help in elucidating the occurrence, enzymatic transformations, and functional roles of these epigenetic/epitranscriptomic nucleobase modifications in DNA and RNA. Shining a light on formylpyrimidines: Mild and orthogonal reaction conditions were established for fluorogenic aldol condensation reactions to generate hemicyanine-like chromophores in DNA and RNA for the residue-specific detection of 5-formyluracil and 5-formylcytosine, which are two naturally occurring oxidized analogues of 5-methylated pyrimidine nucleobases.

BUILDING BLOCKS AND METHODS FOR THE SYNTHESIS OF 5-HYDROXYMETHYLCYTOSINE-CONTAINING NUCLEIC ACIDS

The present invention relates to building blocks and methods for the efficient synthesis of 5-hydroxymethylcytosine-containing nucleic acids such as DNA or RNA.

NUCLEIC ACIDSBUILDING BLOCKS AND METHODS FOR THE SYNTHESIS OF 5-HYDROXYMETHYLCYTOSINE-CONTAINING

The present invention relates to building blocks and methods for the efficient synthesis of 5-hydroxymethylcytosine-containing nucleic acids such as DNA or RNA.