2'-Deoxycytidine monohydrate
[CAS# 951-77-9]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> FMOC-amino acid
• Name: 2'-Deoxycytidine monohydrate
• Synonyms: Deoxycytidine
• Molecular Formula: C₉H₁₃N₃O₄.H₂O
• Molecular Weight: 245.23
• Protein Sequence: C
• CAS Registry Number: 951-77-9
• EC Number: 213-454-1
• SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)O

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 204 °C (Expl.)
• Index of Refraction: 1.72, Calc.^*
• Boiling Point: 497.6±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 254.8±31.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2'-Deoxycytidine monohydrate is a naturally occurring nucleoside and an important component of nucleic acids. It is a derivative of the nucleoside cytidine, where the sugar component is deoxyribose rather than ribose, making it a deoxynucleoside. 2'-Deoxycytidine monohydrate is typically found in DNA, where it pairs with guanine through hydrogen bonding, contributing to the structure and function of DNA molecules.

The discovery of 2'-deoxycytidine dates back to the early studies on the structure of DNA and nucleotides. In these studies, 2'-deoxycytidine was identified as one of the four basic building blocks of DNA, alongside 2'-deoxyadenosine, 2'-deoxyguanosine, and 2'-deoxythymidine. Its unique role in DNA has been extensively studied, as it is involved in the polymerization and replication of DNA strands.

2'-Deoxycytidine monohydrate is typically synthesized through chemical methods that involve the protection and deprotection of the hydroxyl groups in the nucleoside structure, along with selective reactions that introduce the deoxyribose moiety in place of the ribose. The presence of water as a monohydrate in the compound can affect its crystalline form and is typically an outcome of the purification and crystallization process.

The compound has significant biological importance, as it is a precursor in the synthesis of deoxyribonucleic acid (DNA). During DNA replication, 2'-deoxycytidine is incorporated into the growing DNA strand, contributing to the formation of the double helix. The process of DNA synthesis, where 2'-deoxycytidine monohydrate is used as one of the building blocks, is essential for cell division, genetic inheritance, and cellular function.

In medicine, 2'-deoxycytidine and its derivatives have been used in research related to chemotherapy and antiviral therapies. 2'-Deoxycytidine analogs, such as cytarabine, are used as chemotherapy agents for the treatment of certain cancers, particularly hematologic cancers like leukemia. These analogs work by inhibiting DNA synthesis, which ultimately leads to the death of rapidly dividing cancer cells. Cytarabine, for example, is a synthetic analog of 2'-deoxycytidine, where the base is modified to prevent DNA replication, thus interfering with the growth of cancer cells.

Furthermore, 2'-deoxycytidine monohydrate plays a role in the study of nucleotide metabolism and its influence on cellular processes. Research on the metabolism of deoxyribonucleosides like 2'-deoxycytidine has helped scientists understand the mechanisms of DNA repair, replication, and cell cycle regulation.

In terms of practical application, 2'-deoxycytidine monohydrate is used as a standard reagent in the synthesis of nucleotides and nucleic acid analogs in laboratories. It is a fundamental chemical in the field of molecular biology, particularly in the context of DNA sequencing, polymerase chain reaction (PCR), and other molecular biology techniques.

The unique properties of 2'-deoxycytidine, including its role in the structure of DNA and its utility in medical applications such as cancer therapy, continue to make it an essential substance in both research and clinical settings. Its importance in understanding genetic processes and therapeutic applications has been well-established in the scientific community.

References

1989. Maintenance of 5-Methylcytosine in Mammalian Cells by Specific Correction of G/T Mispairs in Favor of Guanine. DNA Damage and Repair.
DOI: 10.1007/978-1-4757-5016-4_21

2012. Cell Fate Control Gene Therapy Based on Engineered Variants of Human Deoxycytidine Kinase. Molecular Therapy, 20(5).
DOI: 10.1038/mt.2011.298

2012. Direct Analysis of 5-Methylcytosine and 5-Methyl-2′-deoxycytidine in Human Urine by Isotope Dilution LC-MS/MS: Correlations with N-Methylated Purines and Oxidized DNA Lesions. Chemical Research in Toxicology, 25(2).
DOI: 10.1021/tx2004954