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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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Properties

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

Description

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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Articles

Discover Bioactive Small Molecules for Gene Regulation

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.

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

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

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