D3897

2′-Deoxycytidine

≥99% (HPLC)

• Synonym(s): Cytosine deoxyriboside
• Empirical Formula (Hill Notation): C₉H₁₃N₃O₄
• CAS Number: 951-77-9
• Molecular Weight: 227.22
• Beilstein/REAXYS Number: 87567
• EC Number: 213-454-1
• MDL number: MFCD00006547
• UNSPSC Code: 41106305
• PubChem Substance ID: 24893793
• NACRES: NA.51

Properties

• biological source: synthetic (organic)
• assay: ≥99% (HPLC)
• form: powder
• solubility: water: 50 mg/mL, clear, colorless to very faintly yellow
• storage temp.: −20°C
• SMILES string: 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
• InChI key: CKTSBUTUHBMZGZ-SHYZEUOFSA-N

Description

General description

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

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)