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Merck

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:
10356-76-0
Molecular Weight:
245.21
NACRES:
NA.77
PubChem Substance ID:
329799711
UNSPSC Code:
12352200
MDL number:
MFCD00077348
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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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

100

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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Certificates of Analysis (COA)

Lot/Batch Number
059K4720V
059K47201
059K4720

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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
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
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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We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

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