I6875
5-Iodocytosine
Synonym(s):
4-Amino-2-hydroxy-5-iodopyrimidine
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About This Item
Empirical Formula (Hill Notation):
C4H4IN3O
CAS Number:
Molecular Weight:
237.00
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
Assay:
≥99% (TLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
formic acid: 50 mg/mL
Storage temp.:
−20°C
InChI
1S/C4H4IN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
SMILES string
[H]N1C=C(I)C(N)=NC1=O
InChI key
UFVWJVAMULFOMC-UHFFFAOYSA-N
biological source
synthetic (organic)
assay
≥99% (TLC)
form
powder
solubility
formic acid: 50 mg/mL
storage temp.
−20°C
Quality Level
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General description
5-Iodocytosine is a modified pyrimidine used in the synthesis of molecules such as pyrrolocytosine and biologically active derivatives.
Application
5-Iodocytosine has been used as iodinated nucleotide with the single crystals of the 3D DNA designed motif for single anomalous dispersion (SAD) studies.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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T S Heuer et al.
Biochemistry, 36(35), 10655-10665 (1997-09-02)
The virally encoded integrase protein carries out retroviral integration, and to do so, it must make specific interactions with both viral and target DNA sequences. The retroviral integrase has three domains: an amino-terminal region of about 50 amino acids that
Y Yoshimura et al.
Bioorganic & medicinal chemistry, 8(7), 1545-1558 (2000-09-08)
As part of our ongoing investigation of the synthesis of biologically interesting 2'-modified-4'-thionucleosides, we synthesized 2'-deoxy-2'-fluoro-4'-thioarabinofuranosylpyrimidine and -purine nucleosides, and evaluated their antiviral and antitumor activities. In the pyrimidine series, beta-anomers of 5-ethyluracil, 5-iodouracil, 5-chloroethyluracil, and 5-iodocytosine derivatives showed potent
R H E Hudson et al.
Nucleosides, nucleotides & nucleic acids, 24(5-7), 581-584 (2005-10-27)
We have employed a tandem Sonogashira/annulation reaction between 5-iodocytosine derivatives and terminal alkynes to yield the fluorescent bicyclic nucleobase pyrrolcytosine. Pyrrolocytosine bearing substituents only on the pyrrole ring are conveniently synthesized from 5-iodocytosine. Water soluble pyrrolocytosines are being investigated as
Chemistry for the synthesis of nucleobase-modified peptide nucleic acid
Hudson RHE, et al.
Pure and Applied Chemistry. Chimie Pure Et Appliquee, 76(7-8), 1591-1598 (2004)
Mouse RS21-C6 is a mammalian 2'-deoxycytidine 5'-triphosphate pyrophosphohydrolase that prefers 5-iodocytosine.
Nonaka M, Tsuchimoto D, et al.
Febs Letters, 276, 1654-1666 (2009)
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