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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)

Quality Level

200

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

Regulatory Information

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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
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
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)
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
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
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