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I2127

Sigma-Aldrich

Isocytosine

≥99%

Synonym(s):

2-Amino-4-hydroxypyrimidine, 2-Aminouracil

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About This Item

Empirical Formula (Hill Notation):
C4H5N3O
CAS Number:
108-53-2
Molecular Weight:
111.10
EC Number:
203-592-0
MDL number:
MFCD00057557
UNSPSC Code:
41106305
PubChem Substance ID:
24895959

biological source

synthetic (organic)

assay

≥99%

form

powder

solubility

acetic acid: 50 mg/mL, clear, colorless

SMILES string

NC1=NC=CC(=O)N1

InChI

1S/C4H5N3O/c5-4-6-2-1-3(8)7-4/h1-2H,(H3,5,6,7,8)

InChI key

XQCZBXHVTFVIFE-UHFFFAOYSA-N

Application

Isocytosine (2-aminouracil) is an isomer of cytosine used in physical chemical studies involving metal complex binding, hydrogen-bonding, and tautomerism and proton transfer effects in nucleobases.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

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

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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A Michael Sismour et al.
Nucleic acids research, 33(17), 5640-5646 (2005-09-30)
Synthetic biology based on a six-letter genetic alphabet that includes the two non-standard nucleobases isoguanine (isoG) and isocytosine (isoC), as well as the standard A, T, G and C, is known to suffer as a consequence of a minor tautomeric
K J LaChance-Galang et al.
Inorganic chemistry, 40(3), 485-492 (2001-02-24)
Pentaammineruthenium moves on ambidentate nitrogen heterocycles by both rotation and linkage isomerization, which may affect the biological activity of potential ruthenium metallopharmaceuticals. The rapid rotation rates of [(NH3)5RuIII] coordinated to the exocyclic nitrogens of isocytosine (ICyt) and 6-methylisocytosine (6MeICyt) have
Deepali Gupta et al.
Inorganic chemistry, 43(11), 3386-3393 (2004-05-25)
Isocytosine (ICH) exists in solution as two major tautomers, the keto form with N1 carrying a proton (1a) and the keto form with N3 being protonated (1b). In water, 1a and 1b exist in equilibrium with almost equal amounts of
Vitaliy Feyer et al.
The journal of physical chemistry. A, 115(26), 7722-7733 (2011-05-20)
Core-level X-ray photoemission and near-edge X-ray absorption fine structure spectra of 5-methylcytosine, 5-fluorocytosine, and isocytosine are presented and discussed with the aid of high-level ab initio calculations. The effects of the methylation, halogenation, and isomerization on the relative stabilities of
X L Yang et al.
Biophysical journal, 75(3), 1163-1171 (1998-09-03)
Isoguanine (2-hydroxyladenine) is a product of oxidative damage to DNA and has been shown to cause mutation. It is also a potent inducer of parallel-stranded DNA duplex structure. The structure of the parallel-stranded DNA duplex (PS-duplex) 5'-d(TiGiCAiCiGiGAiCT) + 5'-d(ACGTGCCTGA), containing
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