240407-53-8

Usage

Uses

Used in Biochemical Research:
[5'-13C]THYMIDINE is used as a tracer molecule for studying the synthesis, incorporation, and metabolism of DNA in biological systems. The 13C isotope provides a unique signature that can be detected and distinguished from unlabeled thymidine, allowing researchers to track DNA replication and repair processes in cells.
Used in Molecular Biology:
[5'-13C]THYMIDINE is used as a labeled nucleotide in techniques such as DNA sequencing and polymerase chain reaction (PCR) to monitor the incorporation of thymidine into newly synthesized DNA strands. This can be particularly useful in studying the fidelity and efficiency of DNA polymerases and other enzymes involved in DNA replication.
Used in Pharmaceutical Industry:
[5'-13C]THYMIDINE is used as a reference compound for the development and quality control of antiviral drugs that target the synthesis of viral DNA. By monitoring the incorporation of labeled thymidine into viral DNA, researchers can assess the effectiveness of these drugs in inhibiting viral replication.
Used in Medical Imaging:
In the field of medical imaging, [5'-13C]THYMIDINE can be used as a labeled compound for positron emission tomography (PET) or magnetic resonance imaging (MRI) to visualize and monitor the proliferation of cells in tumors or other rapidly dividing tissues. This can aid in the diagnosis and treatment planning for various types of cancer.

Upstream product

• 159496-17-0 D-[ribose-13C₅]-5-methyluridine 
• 478511-02-3 C₉⁽¹³⁾CH₁₄N₂O₆ 
• 445433-99-8 2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]ribosylthymine 
• 65-71-4 thymin 
• 184000-88-2 2',3',5'-tri-O-benzoyl[5'-13C]ribosylthymine 
• 445433-95-4 3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5-13C]ribosylthymine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 184000-83-7 methyl 2,3,5-tri-O-benzoyl-D-[5-13C]ribofuranoside 
• 54447-56-2 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-[5-13C]ribose 
• 445434-03-7 3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]thymidine 
• 187589-11-3 C₂₁⁽¹³⁾C₅H₂₇⁽²⁾HN₂O₇ 
• 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 

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

Synthesis of [5'-13C]ribonucleosides and 2'-deoxy[5'-13C]ribonucleosides.

The present efficient synthesis of [5'-13C]ribonucleosides and 2'-deoxy[5'-13C]ribonucleosides is characterized by the synthesis of the D-[5-13C]ribose derivative as an intermediate via the Wittig reaction of 4-aldehydo-D-erythrose dialkyl acetals with Ph3P13CH3I-BuLi to introduce the 13C label at the 5-position of a pentose. This was followed by the highly diastereoselective osmium dihydroxylation for the preparation of 2,3-di-O-benzyl-D-[5-13C]ribose dialkyl acetal and the cyclization from D-[5-13C]ribose dialkyl acetal derivatives to the alkyl D-[5-13C]ribofuranoside derivative by the use of LiBF(4). The obtained D-[5-13C]ribose derivative was converted into [5'-13C]ribonucleosides and subsequently into the corresponding 2'-deoxynucleosides.

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.