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I6875

Sigma-Aldrich

5-Iodocytosine

Synonym(s):

4-Amino-2-hydroxy-5-iodopyrimidine

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About This Item

Empirical Formula (Hill Notation):
C4H4IN3O
CAS Number:
1122-44-7
Molecular Weight:
237.00
MDL number:
MFCD00023162
UNSPSC Code:
41106305
PubChem Substance ID:
24896095
NACRES:
NA.51

biological source

synthetic (organic)

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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