D3897
2′-Deoxycytidine
≥99% (HPLC), synthetic (organic), powder
Synonym(s):
Cytosine deoxyriboside
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About This Item
Empirical Formula (Hill Notation):
C9H13N3O4
CAS Number:
Molecular Weight:
227.22
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
213-454-1
MDL number:
Beilstein/REAXYS Number:
87567
Product Name
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
Related Categories
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.
Storage Class
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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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
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.
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
Urinary Nucleosides and Deoxynucleosides
Patejko M, et al.
Advances in Clinical Chemistry, 83, 1-51 (2018)
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
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