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Merck
CN

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:
Molecular Weight:
111.10
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
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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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

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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Raffaele Saladino et al.
Journal of the American Chemical Society, 130(46), 15512-15518 (2008-10-23)
We describe the one-pot synthesis of a large panel of nucleic bases and related compounds from formamide in the presence of iron sulfur and iron-copper sulfur minerals as catalysts. The major products observed are purine, 1H-pyrimidinone, isocytosine, adenine, 2-aminopurine, carbodiimide
Agota Aučynaitė et al.
Frontiers in microbiology, 9, 2375-2375 (2018-10-24)
Cytosine is one of the four letters of a standard genetic code, found both in DNA and in RNA. This heterocyclic base can be converted into uracil upon the action of the well-known cytosine deaminase. Isocytosine (2-aminouracil) is an isomer
Philip D Edwards et al.
Journal of medicinal chemistry, 50(24), 5912-5925 (2007-11-08)
Fragment-based lead generation has led to the discovery of a novel series of cyclic amidine-based inhibitors of beta-secretase (BACE-1). Initial fragment hits with an isocytosine core having millimolar potency were identified via NMR affinity screening. Structure-guided evolution of these fragments
T M Chin et al.
Biochemistry, 39(40), 12457-12464 (2000-10-04)
The formation of a DNA "paper-clip" type triple helix (triplex) with a common sequence 5'-d-(TC)(3)T(a)()(CT)(3)C(b)()(AG)(3) (a and b = 0-4) was studied by UV thermal melting experiments and CD spectra. These DNA oligomers form triplexes and duplexes under slightly acidic
Rumyana I Bakalska et al.
Journal of molecular modeling, 18(12), 5133-5146 (2012-07-11)
An experimental and theoretical investigation was performed to study the photostability of cytosine and isocytosine. The experimental UV irradiation of acetonitrile solutions of the two compounds showed that the amino-oxo tautomer of cytosine is photostable while the amino-oxo tautomer of

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