185553-96-2

Usage

Uses

Used in Biochemical Research:
[2'-13C]THYMIDINE is used as a tracer for studying the synthesis, incorporation, and metabolism of DNA in biological systems. The 13C labeling enables researchers to track the behavior of this nucleoside within cells and monitor its interactions with other cellular components.
Used in Medical Diagnostics:
[2'-13C]THYMIDINE is used as a diagnostic tool for detecting and monitoring the progression of diseases that involve changes in DNA synthesis, such as cancer. The labeled thymidine can be used to measure the rate of DNA replication in cells, providing valuable information about the aggressiveness and potential treatment response of the disease.
Used in Pharmaceutical Development:
[2'-13C]THYMIDINE is used as a research compound in the development of new drugs targeting DNA synthesis and repair pathways. The labeled thymidine can be employed to study the mechanism of action of potential therapeutic agents and to optimize their efficacy and selectivity.
Used in Radiotracer Studies:
[2'-13C]THYMIDINE is used as a radiotracer in positron emission tomography (PET) and other imaging techniques to visualize and quantify DNA synthesis in vivo. This application can be particularly useful in the study of tumor growth and the evaluation of the effectiveness of cancer treatments.
Used in Forensic Science:
[2'-13C]THYMIDINE can be used as a forensic tool to analyze biological samples, such as blood or tissue, to determine the age of the sample or to identify specific DNA sequences. The 13C labeling provides a unique signature that can be used to distinguish between different sources of DNA.
Used in Environmental Science:
[2'-13C]THYMIDINE can be employed in environmental studies to investigate the impact of pollutants or other environmental factors on the DNA synthesis of microorganisms or other organisms. This information can be used to assess the health of ecosystems and to develop strategies for environmental remediation.

Upstream product

• 65-71-4 thymin 
• 187589-10-2 C₁₈⁽¹³⁾C₅H₂₅⁽²⁾HO₇ 
• 187589-09-9 C₁₀⁽¹³⁾C₅H₁₉⁽²⁾HO₅ 
• 159496-09-0 [13C5]-1,2-di-O-acetyl-3,5-di-O-benzoyl-α,β-D-ribofuranose 
• 159496-08-9 C₄⁽¹³⁾C₅H₁₆O₇S 
• 503173-76-0 [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)-5-methyluracil 
• 666824-07-3 C₁₇⁽¹³⁾C₅H₄₀N₂O₇Si₂ 
• 666824-08-4 C₁₇⁽¹³⁾C₅H₄₀N₂O₆Si₂ 
• 159496-17-0 D-[ribose-13C₅]-5-methyluridine 
• 187589-11-3 C₂₁⁽¹³⁾C₅H₂₇⁽²⁾HN₂O₇ 

Relevant academic research and scientific papers

NMR Spectroscopic Determination of the Solution Structure of a Branched Nucleic Acid from Residual Dipolar Couplings by Using Isotopically Labeled Nucleotides

Only a small set of magnetic-field-induced residual dipolar couplings is required to determine the global structure of branched nucleic acids. This is demonstrated for the example of the Holliday junction (shown schematically) after 13C labelin

One-pot two-step enzymatic coupling of pyrimidine bases to 2-deoxy-D-ribose-5-phosphate. A new strategy in the synthesis of stable isotope labeled deoxynucleosides

The enzymatic synthesis of thymidine from 2-deoxy-D-ribose-5-phosphate is achieved, in a one-pot two-step reaction using phosphoribomutase (PRM) and commercially available thymidine phosphorylase (TP). In the first step the sugar-5-phosphate is enzymatically rearranged to α-2-deoxy-D-ribose-1-phosphate. Highly active PRM is easily obtained from genetically modified overproducing E. coli cells (12000 units/84 mg protein) and is used without further purification. In the second step thymine is coupled to the sugar-1-phosphate. The thermodynamically unfavorable equilibrium is shifted to the product by addition of MnCl2 to precipitate inorganic phosphate. In this way the overall yield of the β-anomeric pure nucleoside increases from 14 to 60%. In contrast to uracil, cytosine is not accepted by TP as a substrate. Therefore, 2′-deoxy-cytidine is obtained by functional group transformations of the enzymatically prepared 2′-deoxy-uridine. The method has been demonstrated by the synthesis of [2′,5′-13C2]- and [1′,2′,5′-13C3]thymidine as well as [1′,2′,5′-13C3]2′-deoxyuridine and [3′,4′-13C2]2′-deoxycytidine. In addition the nucleoside bases thymine and uracil are tetralabeled at the (1,3-15N2,2,4-13C2)-atomic positions. All compounds are prepared without any scrambling or dilution of the labeled material and are thus obtained with a very high isotope enrichment (96-99%). In combination with the methods that have been developed earlier it is concluded that each of the 13C- and 15N-positions and combination of positions of the pyrimidine deoxynucleosides can be efficiently labeled starting from commercially available and highly 13C- or 15N-enriched formaldehyde, acetaldehyde, acetic acid, potassium cyanide, methylamine hydrochloride, and ammonia.

Synthesis of (5'S)-1;1',2',3',4',5'-13C5>-Thymidine via Stereoselective Deuteration of a 5-Oxoribose Derivative

(5'S)-1:1',2'3'4'5'-13C5>-Thymidine has been synthesized by a stereoselective deuteride transfer reaction from (-)- or (+)-1>-isobornyloxymagnesium bromide to a 5-oxoribose derivative, which can be readily prepared from 6>-D-glucose.The overall yield from D-glucose to thymidine was 27percent.The various nucleosides with a stereoselective 2H-label together with 13C at the C5' position, which have become available by the present method, will be quite useful for stereospecific assignment of the diastereotopic C5' methylene signals, and also for conformational analyses of the O5'-C5' bonds in nucleic acid oligomers.

Chemical Synthesis of 13C-labelled Monomers for the Solid-Phase and Template Controlled Enzymatic Synthesis of DNA and RNA Oligomers

The preparation of 13C-labelled ribonucleosides starting from -glucose 1 and the corresponding nucleobases 5a-e or 6a-e (N6-benzoyl-adenine, N2-acetyl-guanine, N4-benzoyl-cytosine, uracil and thymine) in 47-66percent overall yield is described.Their subsequent transformation into 5'-O-dimethoxytrityl protected DNA-phosphoramidites and 5'-O-dimethoxytrityl-2'-O-trialkylsilyl protected RNA-phosphor-amidites for the solid phase synthesis of DNA- and RNA-oligomers and to 5'-O-ribo- and deoxyribo-nucleosidetriphosphates for template controlled enzymatic synthesis (polymerase- or reverse transcriptase reaction) has been carried out.