F5307

5−Fluoro−2′−deoxycytidine

Name: 5−Fluoro−2′−deoxycytidine
Brand: SIGMA
Price: 2609.5 CZK

≥98% (HPLC), powder

Synonym(s):

2′-deoxy-5-fluoro-Cytidine, FCDR, FdCyd

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5 MG

CZK 2,609.50

25 MG

CZK 10,030.00

CZK 2,609.50

List PriceCZK 3,070.00Save 15%

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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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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

Bioactive Small Molecule Inhibitors

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Show Differences

1 of 4

This Item	D6571	SML0653	G6423
Sigma-Aldrich F5307 5−Fluoro−2′−deoxycytidine	Sigma-Aldrich D6571 3′,4′-Dimethoxyflavone	Sigma-Aldrich SML0653 Capecitabine	Sigma-Aldrich G6423 Gemcitabine hydrochloride
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form powder	form powder	form powder	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. room temp	storage temp. room temp	storage temp. 2-8°C	storage temp. room temp
solubility DMSO: >20 mg/mL	solubility DMSO: ≥20 mg/mL	solubility H₂O: 10 mg/mL, clear (warmed)	solubility H₂O: ≥10 mg/mL
color white to off-white	color white to off-white	color white to beige	color -

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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Crystallization and preliminary crystallographic analysis of a DNA (cytosine-5)-methyltransferase from Haemophilus aegyptius bound covalently to DNA.

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

A mutant HpaII methyltransferase functions as a mutator enzyme.

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

Sequence-specific and mechanism-based crosslinking of Dcm DNA cytosine-C5 methyltransferase of E. coli K-12 to synthetic oligonucleotides containing 5-fluoro-2'-deoxycytidine.

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

Recognition of the highly conserved YMDD region in the human immunodeficiency virus type 1 reverse transcriptase by HLA-A2-restricted cytotoxic T lymphocytes from an asymptomatic long-term nonprogressor.

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

Micronuclei induced by modulators of methylation: analogs of 5-azacytidine.

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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5−Fluoro−2′−deoxycytidine