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Merck

D3897

2′-Deoxycytidine

≥99% (HPLC), synthetic (organic), powder

Synonyme(s) :

Cytosine deoxyriboside

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About This Item

Formule empirique (notation de Hill) :
C9H13N3O4
Numéro CAS:
951-77-9
Poids moléculaire :
227.22
NACRES:
NA.51
PubChem Substance ID:
24893793
UNSPSC Code:
41106305
EC Number:
213-454-1
MDL number:
MFCD00006547
Beilstein/REAXYS Number:
87567

Nom du produit

2′-Deoxycytidine, ≥99% (HPLC)

InChI key

CKTSBUTUHBMZGZ-SHYZEUOFSA-N

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

SMILES string

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

biological source

synthetic (organic)

assay

≥99% (HPLC)

form

powder

solubility

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

storage temp.

−20°C

Quality Level

200

Catégories apparentées

Application

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

Biochem/physiol Actions

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.

General description

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000509941
0000509941
0000509943
0000509942
0000509942

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Consulter la Bibliothèque de documents

Urinary Nucleosides and Deoxynucleosides
Patejko M, et al.
Advances in Clinical Chemistry, 83, 1-51 (2018)
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.
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
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
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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