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
• Article Data: 7

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

2-Thiothymidine is a mRNA therapy used for treatment of ornithine transcarbamylase deficiency.

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

• 636-26-0 5-methyl-2-thiouracil 
• 50-89-5 thymidine 
• 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 
• 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.

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.

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