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D3897

Sigma-Aldrich

2′-Deoxycytidine

≥99% (HPLC)

Sinonimo/i:

Cytosine deoxyriboside

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About This Item

Formula empirica (notazione di Hill):
C9H13N3O4
Numero CAS:
951-77-9
Peso molecolare:
227.22
Beilstein:
87567
Numero CE:
213-454-1
Numero MDL:
MFCD00006547
Codice UNSPSC:
41106305
ID PubChem:
24893793
NACRES:
NA.51

Origine biologica

synthetic (organic)

Saggio

≥99% (HPLC)

Forma fisica

powder

Solubilità

water: 50 mg/mL, clear, colorless to very faintly yellow

Temperatura di conservazione

−20°C

Stringa SMILE

NC1=NC(=O)N(C=C1)[C@H]2C[C@H](O)[C@@H](CO)O2

InChI

1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
CKTSBUTUHBMZGZ-SHYZEUOFSA-N

Categorie correlate

Descrizione generale

2′-Deoxycytidine (deoxyC) is one of the deoxynucleosides containing cytosine as the nucleobase. It is found in the blood, feces, and urine.

Applicazioni

2′-Deoxycytidine has been used:
  • as a substrate for Trypanosoma brucei cytidine deaminase (TbCDA) to measure its activity
  • as a standard in the isolation and quantification of metabolite levels in murine tumor interstitial fluid by liquid chromatography-mass spectrometry (LC–MS)
  • to study the role of autophagy in response to oncogenes and DNA replication stress

Azioni biochim/fisiol

2′-Deoxycytidine (deoxyC) forms dCTP upon phosphorylation which is used to synthesis DNA via various DNA polymerases or reverse transcriptases. DeoxyC is the substrate for deoxycytidine deaminase (EC 3.5.4.14) which converts it into 2′-deoxyuridine. DeoxyC is phosphorylated to the nucleotide dCMP by the enzyme deoxycytidine kinase (DCK). DeoxyC serves as a potential head and neck cancer marker.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Sigma-Aldrich

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5-Methylcytidine ≥99%

Sigma-Aldrich

M4254

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5′-Deoxyadenosine methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase substrate

Sigma-Aldrich

D1771

5′-Deoxyadenosine

2′-Deoxycytidine 5′-triphosphate disodium salt ≥95%

Sigma-Aldrich

D4635

2′-Deoxycytidine 5′-triphosphate disodium salt

Martyna Modrzejewska et al.
Free radical biology & medicine, 101, 378-383 (2016-11-12)
The most plausible mechanism behind active demethylation of 5-methylcytosine involves TET proteins which participate in oxidation of 5-methylcytosine to 5-hydroxymethylcytosine; the latter is further oxidized to 5-formylcytosine and 5-carboxycytosine. 5-Hydroxymethyluracil can be also generated from thymine in a TET-catalyzed process.
Urinary Nucleosides and Deoxynucleosides
Patejko M, et al.
Advances in Clinical Chemistry, 83, 1-51 (2018)
Megan Beetch et al.
Scientific reports, 10(1), 2415-2415 (2020-02-14)
Triple-negative breast cancer (TNBC) is a subtype of breast cancer unresponsive to traditional receptor-targeted treatments, leading to a disproportionate number of deaths. Invasive breast cancer is believed to evolve from non-invasive ductal carcinoma in situ (DCIS). Detection of triple-negative DCIS
Ana Moro-Bulnes et al.
mSphere, 4(4) (2019-08-09)
Cytidine deaminase (CDA) is a pyrimidine salvage enzyme that catalyzes cytidine and deoxycytidine hydrolytic deamination to yield uridine and deoxyuridine. Here we report the biochemical characterization of Trypanosoma brucei CDA as an enzyme within the tetrameric class of the CDA
Santiago Uribe-Lewis et al.
Genome biology, 16, 69-69 (2015-04-09)
The discovery of cytosine hydroxymethylation (5hmC) as a mechanism that potentially controls DNA methylation changes typical of neoplasia prompted us to investigate its behaviour in colon cancer. 5hmC is globally reduced in proliferating cells such as colon tumours and the
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