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
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
Recommended Products
biological source
synthetic (organic)
Quality Level
Assay
≥99% (TLC)
form
powder
solubility
formic acid: 50 mg/mL
storage temp.
−20°C
SMILES string
[H]N1C=C(I)C(N)=NC1=O
InChI
1S/C4H4IN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChI key
UFVWJVAMULFOMC-UHFFFAOYSA-N
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
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)
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
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
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)
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