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F5307

5−Fluoro−2′−deoxycytidine

Name: 5−Fluoro−2′−deoxycytidine
Brand: SIGMA

≥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

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Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

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

InChI key

IDYKCXHJJGMAEV-RRKCRQDMSA-N

Related Categories

Bioactive Small Molecule Inhibitors

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

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

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

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

Stability of 5-fluoro-2'-deoxycytidine and tetrahydrouridine in combination.

Duoli Guo et al.

AAPS PharmSciTech, 11(1), 247-252 (2010-02-13)

In vivo, the DNA methyltransferase inhibitor, 5-fluoro-2'-deoxycytidine (FdCyd, NSC-48006), is rapidly converted to its unwanted metabolites. Tetrahydrouridine (THU, NSC-112907), a cytidine deaminase inhibitor can block the first metabolic step in FdCyd catabolism. Clinical studies have shown that co-administration with THU

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Global Trade Item Number

SKU	GTIN
F5307-25MG	04061832631998
F5307-5MG	04061832632001

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