2'-Deoxycytidine CAS No. 951-77-9

Product Description

2'-Deoxycytidine is a nucleoside that plays a vital role in the structure and function of DNA. It consists of a cytosine base attached to a 2'-deoxyribose sugar, lacking a hydroxyl group at the 2' position, which distinguishes it from ribose in RNA. It appears as a white crystalline powder. It is soluble in water and has a melting point of around 210–215 °C, at which it decomposes. 2'-Deoxycytidine is a fundamental building block of DNA, pairing with deoxyguanosine via hydrogen bonds. It is essential for DNA synthesis and replication in living cells. In addition to its biological role, 2'-deoxycytidine is used in molecular biology and as a precursor in the synthesis of antiviral and anticancer drugs, such as cytarabine. It is also a natural metabolite found in various organisms, including humans, yeast, and E. coli. Its analogues, like decitabine, are used in cancer treatment as DNA methyltransferase inhibitors. Furthermore, specific modified forms of 2'-deoxycytidine can serve as biomarkers for certain diseases, such as breast cancer.

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Product Use & Characteristics

Properties

• Molecular Formula: C₉H₁₃N₃O₄

• Molecular Weight: 227.22 g/mol

• Appearance: White crystalline powder.

• Solubility: Soluble in water, slightly soluble in methanol.

• Melting Point: ~210–215 °C (decomposes).

• Stability: Stable under normal conditions; light-sensitive.

Structure and Composition

• Chemical Class: Nucleoside.

• Components:

  • Base: Cytosine (a pyrimidine base).

  • Sugar: 2'-Deoxyribose (a five-carbon sugar without a hydroxyl group at the 2' position).

• Structural Formula: Cytosine ring attached to the 1' position of 2'-deoxyribose via a β-N1-glycosidic bond.

Uses

• DNA Synthesis: A crucial precursor for DNA synthesis. It gets phosphorylated by enzymes like deoxycytidine kinase (DCK) to form deoxycytidine monophosphate (dCMP), which can then be further converted to dCTP, a building block for DNA.

• Metabolite: A natural metabolite found in humans, as well as in organisms like Saccharomyces cerevisiae (yeast) and Escherichia coli.

• Research Applications:

  • Inhibitor: Can inhibit the biological effects of Bromodeoxyuridine (BrdU), a synthetic nucleoside analog used in cell proliferation studies.

  • Cancer Research: Its analogue, 5-aza-2'-deoxycytidine (decitabine), is an approved drug for myelodysplastic syndromes (MDS). Decitabine acts as a DNA methyltransferase inhibitor.

  • Biomarker: Specific modified forms of 2'-deoxycytidine (e.g., 5-hydroxymethyl-2'-deoxycytidine) can serve as biomarkers for certain conditions, such as breast cancer.

  • Metabolic Disorder Treatment: Research suggests that 2'-deoxycytidine may be beneficial in treating thymidine kinase 2 (TK2) deficiency, a metabolic disorder.

• Pharmaceutical Applications:

  • Antiviral and Anticancer Drugs: Used as a precursor in the synthesis of antiviral and anticancer drugs (e.g., cytarabine, gemcitabine).

  • Biomarker in Nucleoside Metabolism Studies: Used in studies related to nucleoside metabolism.

  • Component in Molecular Biology Protocols: Used in PCR, DNA sequencing, and other molecular biology protocols.

Biosynthesis and Metabolism

• Degradation: Converted into cytosine and deoxyribose by nucleoside phosphorylases or deaminated to form 2'-deoxyuridine.

• Synthesis Methods: Can be chemically synthesized or extracted from DNA hydrolysates.

Related Compounds

• Cytidine: A ribonucleoside containing a complete ribose (with –OH at the 2' position).

• dCMP (2'-deoxycytidine monophosphate): 2'-Deoxycytidine plus a phosphate group.

• dCTP (Deoxynucleoside triphosphate): A raw material for DNA synthesis.

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