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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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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
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