22003-31-2

Usage

Chemical Family

Pyrimidine nucleoside

Structural Components

Pyrimidine ring and a ribosyl or deoxyribosyl group

Role

Synthesis and function of nucleic acids (DNA and RNA)

Biological Processes

Cell signaling, metabolism, and gene expression

Pharmaceutical Use

Building block for antiviral and anticancer drugs

InChI:InChI=1/C10H14N2O4/c1-6-3-11-10(15)12(4-6)9-2-7(14)8(5-13)16-9/h3-4,7-9,13-14H,2,5H2,1H3/t7-,8+,9-/m0/s1

Upstream product

• 385843-34-5 3',5'-O-bis(triethylsilyl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one 
• 883868-32-4 3',5'-bis(O-tert-butyldimethylsilyl)-N¹-(β-D-2'-deoxyribosyl)-5-methyl-pyrimidin-2-one 
• 1053254-87-7 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-4-hydrazino-5-methyl-1H-pyrimidin-2-one 
• 80991-40-8 1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tertbutyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 50-89-5 thymidine 
• 385843-32-3 3',5'-O-bis(triethylsilyl)thymidine 
• 385843-33-4 3',5'-O-bis(triethylsilyl)-4-(1,2,4-triazolo)thymidine 
• 97626-18-1 1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]thymine 

Downstream Products

• 125258-59-5 5'-O-(4,4'-dimethoxytrityl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one 
• 1363821-34-4 C₄₉H₅₄N₅O₁₅P 
• 1363821-31-1 1-[5-O-(4,4'-dimethoxytrityl)-3-O-levulinyl-2-deoxy-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone 

Relevant academic research and scientific papers

Photosensitization of DNA by 5-methyl-2-pyrimidone deoxyribonucleoside: (6 - 4) photoproduct as a possible trojan horse

A (photo)sensitive subject: Combined agarose gel electrophoresis and photochemical studies show that 5-methyl-2-pyrimidone (see picture), the main chromophore of (6-4) photoproducts, behaves as a DNA photosensitizer. These results raise the question of whether the (6-4) lesions can act as Trojan horses, enhancing cyclobutane pyrimidine dimer (CPD) formation and oxidative damage. Copyright

Synthesis and properties of fluorescent cycloSal nucleotides based on the pyrimidine nucleoside m5K and its 2′,3′-dideoxy analog dm5K

The synthesis of the fluorescent thymidine nucleoside analog 5-methyl-pyrimidin-2-one nucleoside 1 (m5K) and that of its 2′,3′-dideoxy derivative 2 (dm5K) are described. Moreover, the conversion of 1 and 2 into the corresponding 3-methyl-cycloSal- phosphate triesters 11 and 12 or an enzyme-cleavable prodrug 5-acetoxymethylpropionate-cycloSal-phosphate triester 13, and the fluorescence and hydrolysis properties of these new lipophilic triesters are reported. Finally, the suitability of these cycloSal pronucleotides as probes is demonstrated in a cell-extract hydrolysis experiment and a model study for cell uptake. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Facile synthesis of a fluorescent deoxycytidine analogue suitable for probing the RecA nucleoprotein filament

equation presented We report the synthesis of the fluorescent 2′-deoxycytidine analogue 5-methylpyrimidin-2-one nucleoside, its incorporation at three specified sites in a single 60-nucleotide DNA molecule, and the use of its total and polarized intrinsic