F5307
5−Fluoro−2′−deoxycytidine
≥98% (HPLC), powder
Synonym(s):
2′-deoxy-5-fluoro-Cytidine, FCDR, FdCyd
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About This Item
Empirical Formula (Hill Notation):
C9H12FN3O4
CAS Number:
Molecular Weight:
245.21
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Product Name
5−Fluoro−2′−deoxycytidine, ≥98% (HPLC), powder
InChI key
IDYKCXHJJGMAEV-RRKCRQDMSA-N
SMILES string
NC1=NC(=O)N(C=C1F)[C@H]2C[C@H](O)[C@@H](CO)O2
InChI
1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1
assay
≥98% (HPLC)
form
powder
color
white to off-white
solubility
DMSO: >20 mg/mL
storage temp.
room temp
Quality Level
Related Categories
Biochem/physiol Actions
5-Fluoro-2′-deoxycytidine is a mechanism based DNMT (DNA cytosine-5 methyltransferase) inhibitor, that forms a covalent link with the cysteine residue in the active site of DNMT.
Features and Benefits
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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J C Shen et al.
Nucleic acids research, 23(21), 4275-4282 (1995-11-11)
DNA (cytosine-5)-methyltransferases can cause deamination of cytosine when the cofactor S-adenosylmethionine (AdoMet) is limiting and thus function as sequence-specific C-->U mutator enzymes. Here we explored whether mutations causing inactivation of the cofactor binding activity of the HpaII methyltransferase, thus mimicking
K M Reinisch et al.
Journal of molecular biology, 238(4), 626-629 (1994-05-13)
A DNA (cytosine)-5-methyltransferase from Haemophilus aegyptius (M.Hae III), which catalyzes methyl transfer from S-adenosyl-L-methionine to DNA, has been crystallized as a covalent complex with a suicide oligonucleotide substrate. Crystals of the co-complex were grown by vapor diffusion with hanging droplets
T Hanck et al.
Nucleic acids research, 21(2), 303-309 (1993-01-25)
The product of the dcm gene is the only DNA cytosine-C5 methyltransferase of Escherichia coli K-12; it catalyses transfer of a methyl group from S-adenosyl methionine (SAM) to the C-5 position of the inner cytosine residue of the cognate sequence
E Harrer et al.
The Journal of infectious diseases, 173(2), 476-479 (1996-02-01)
The human immunodeficiency virus (HIV) type 1 reverse transcriptase (RT) is an important target for therapeutic intervention and for HIV-1-specific cytotoxic T lymphocytes (CTL). An HLA-A2-restricted CTL epitope containing the sequence YMDD, which is highly conserved among human and animal
H Stopper et al.
Carcinogenesis, 16(7), 1647-1650 (1995-07-01)
Jones and coworkers demonstrated a qualitative correlation between 5-azacytidine and some of its analogs in inducing changes in cell morphology and their ability in preventing DNA methylation. Previously, we evaluated the same compounds to determine their ability to induce trifluorothymidine
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