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:
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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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.
General description
5-Iodocytosine is a modified pyrimidine used in the synthesis of molecules such as pyrrolocytosine and biologically active derivatives.
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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Uwe Pieper et al.
Biochemistry, 41(16), 5245-5254 (2002-04-17)
The GTP-dependent restriction enzyme McrBC consists of two polypeptides: one (McrB) that is responsible for GTP binding and hydrolysis as well as DNA binding and another (McrC) that is responsible for DNA cleavage. It recognizes two methylated or hemimethylated RC
S Harinipriya et al.
Journal of colloid and interface science, 250(1), 201-212 (2005-11-18)
The two-dimensional condensation behavior exhibited by nucleobases at a mercury/aqueous solution interface is analyzed on the basis of their hydrogen-bonded quadruplex structures, and the experimentally observed critical temperatures are rationalized incorporating different types of hydrogen bonding, surface coordination effects, and
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)
R H E Hudson et al.
Nucleosides, nucleotides & nucleic acids, 22(5-8), 1029-1033 (2003-10-21)
The Pd0/Cu1 catalyzed cross-coupling of terminal alkynes onto peptide nucleic acid monomers or submonomers bearing iodinated nucleobases has been utilized as a route to base-modified oligomers. Both 5-iodouracil and 5-iodocytosine derivatives undergo the cross-coupling to give the expected products in
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
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