28585-51-5

Basic information

• Product Name: 2-THIOTHYMIDINE
• Synonyms: 2-THIOTHYMIDINE;1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2-sulfanylidenepyrimidin-4-one;2-Thio-2'-deoxythymidine
• CAS NO: 28585-51-5
• Molecular Formula: C₁₀H₁₄N₂O₄S
• Molecular Weight: 258.29
• Mol File: 28585-51-5.mol

Chemical Properties

• Appearance: /
• Density: 1.52 g/cm³
• Refractive Index: 1.672
• CAS DataBase Reference: 2-THIOTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-THIOTHYMIDINE(28585-51-5)
• EPA Substance Registry System: 2-THIOTHYMIDINE(28585-51-5)

Safety Data

• Hazardous Substances Data: 28585-51-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Thiothymidine is used as a therapeutic agent for the treatment of ornithine transcarbamylase (OTC) deficiency, a genetic disorder characterized by the inability to properly metabolize ammonia in the body. As a component of mRNA therapy, it helps in the development of personalized treatments that can potentially correct the genetic defect and alleviate the symptoms associated with the condition.
In addition to its application in treating OTC deficiency, 2-Thiothymidine may also hold potential for other therapeutic uses due to its unique chemical properties. However, further research and development are necessary to explore and validate its potential applications in various medical and biotechnological fields.

InChI:InChI=1/C10H14N2O4S/c1-5-3-12(10(17)11-9(5)15)8-2-6(14)7(4-13)16-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,17)/t6-,7+,8+/m0/s1

Upstream product

• 125258-60-8 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 28585-50-4 3’-O-acetyl-2’-deoxy-2-thiothymidine 
• 59211-01-7 3’-O-acetyl-2,5’-anhydrothymidine 
• 15425-09-9 3,5'-cyclo-2'-deoxyguanosine 
• 636-26-0 5-methyl-2-thiouracil 
• 50-89-5 thymidine 
• 151503-25-2 3'-p-toluoyl-2-thiothymidine 

Downstream Products

• 1213779-12-4 1-(2'-deoxy-5'-O-4,4'-dimethoxytrityl-β-D-erythro-ribofuranosyl)-2-methylthiothymine 
• 125258-60-8 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 125258-63-1 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 144988-68-1 5’-O-(4,4’-dimethoxytrityl)-2’-deoxy-5-methyl-4-pyrimidinone 2-cyanoethyl N,N-diisopropylphosphoramidite 
• 151503-27-4 5’-O-(4,4’-dimethoxytrityl)-2’-deoxy-5-methyl-4-pyrimidinone 

Relevant articles and documents

Selenium or thiothymine nucleoside-5 '-triphosphoric acid and synthesis method thereof

The invention discloses selenium or thiothymine nucleoside-5 '-triphosphoric acid and a synthesis method of the selenium or thiothymine nucleoside-5'-triphosphoric acid. The synthesis method comprises the following partial synthesis steps: a deprotection reaction is carried out on a compound 3 or 1 and trichloroacetic acid to respectively obtain SeT (namely 4Se) or ST (namely 4S); then, the compound 4Se and the compound 4S are respectively converted into a compound 5Se and a compound 5S through a one-pot synthesis method, SeTTP is the compound 5Se, and STTP is the compound 5S; next, the compounds 5Se and 5S are purified, the purified compounds 5Se and 5S are characterized to confirm the structure and purity of the compounds 5Se and 5S, and then DNA enzymatic synthesis is carried out by using SeTTP or STTP and DNA polymerase to obtain a compound 6, namely Se-DNA or S-DNA or selenium sulfo Se/S-DNA; according to the invention, a selenium or sulfur atom specific modification strategy SAM is established by innovatively synthesizing SeTTP and STTP and innovatively synthesizing DNA polymerase, so that T/G mismatch in DNA polymerization is inhibited, the specificity of base pairing is improved, and the SAM method is proved to be capable of improving the accuracy and sensitivity of polymerase reaction, nucleic acid molecule recognition and molecule detection.

Fluorescent labeling of s2T-incorporated DNA and m5s2U-modified RNA

We report herein comprehensive investigations of alkylation/sulfur exchange reactions of sulfur-containing substrates including nucleosides such as s2U, m5s2U, s4U, s2A and s2T-incorporated DNA enable by comprehensive screenings of the reagents (2a–2h). It has been proven that iodoacetamide (2a) displays the most promising feasibility toward sulfur-containing substrates including s2T, s2U, m5s2U, s4U and s2A. In sharp contrast, the alkylation process with S-benzyl methanethiosulfonate (BMTS, 2h) displays the best application potential only for s4U. Based on these results, the fluorescent labeling of s2T-incorporated DNA and m5s2U-modified RNA has been achieved. Supplemental data for this article is available online at https://doi.org/10.1080/15257770.2021.1942044.

Polymerase recognition of 2-thio-iso-guanine·5-methyl-4-pyrimidinone (iGs·P) - A new DD/AA base pair

Polymerase specificity is reported for a previously unknown base pair with a non-standard DD/AA hydrogen bonding pattern: 2-thio-iso-guanine·5-methyl-4-pyrimidinone. Our findings suggest that atomic substitution may provide a solution for low fidelity previously associated with enzymatic copying of iso-guanine.

One-pot approach to functional nucleosides possessing a fluorescent group using nucleobase-exchange reaction by thymidine phosphorylase

Herein, we describe β-selective coupling between a modified uracil and a deoxyribose to produce functionalized nucleosides catalyzed by thymidine phosphorylase derived from Escherichia coli. This enzyme mediates nucleobase-exchange reactions to convert unnatural nucleosides possessing a large functional group such as a fluorescent molecule, coumarin or pyrene, linked via an alkyl chain at the C5 position of uracil. 5-(Coumarin-7-oxyhex-5- yn)uracil (C4U) displayed 57.2% conversion at 40% DMSO concentration in 1.0 mM phosphate buffer pH 6.8 to transfer thymidine to an unnatural nucleoside with C4U as the base. In the case of using 5-(pyren-1-methyloxyhex-5-yn)uracil (P4U) as the substrate, TP also could catalyse the reaction to generate a product with a very large functional group at 50% DMSO concentration (21.6% conversion). We carried out docking simulations using MF myPrest for the modified uracil bound to the active site of TP. The uracil moiety of the substrate binds to the active site of TP, with the fluorescent moiety linked to the C5 position of the nucleobase located outside the surface of the enzyme. As a consequence, the bulky fluorescent moiety binding to uracil has little influence on the coupling reaction.

Importance of 3′-hydroxyl group of the nucleosides for the reactivity of thymidine phosphorylase from Escherichia coli

Thymidine phosphorylase in phosphate buffer catalyzed the conversion of thymidine to unnatural nucleosides. The 3′-OH, but not the 5′-OH of ribosyl moiety is necessary to be recognized as a substrate. Thus 3′-deoxythymidine could not convert to 5-fluorouracil-2′,3′- dideoxyribose. However, 5′-deoxythymidine was converted to 5-fluorouracil-2′,5′-dideoxyribose. Copyright

Efficient desulfurization of 2-thiopyrimidine nucleosides to the corresponding 4-pyrimidinones

A procedure is described for the preparation of 2'-deoxy-4-pyrimidinone (dH2U) and 2'-deoxy-5-methyl-4-pyrimidinone (dH2T) nucleosides. The key transformation is a nearly quantitative desulfurization of the corresponding 2-thio analo