125258-59-5

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one
• Synonyms: 5'-O-(4,4'-dimethoxytrityl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one
• CAS NO: 125258-59-5
• Molecular Weight: 528.605
• Mol File: 125258-59-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one(125258-59-5)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one(125258-59-5)

Safety Data

• Hazardous Substances Data: 125258-59-5(Hazardous Substances Data)

Upstream product

• 385843-33-4 3',5'-O-bis(triethylsilyl)-4-(1,2,4-triazolo)thymidine 
• 385843-32-3 3',5'-O-bis(triethylsilyl)thymidine 
• 385843-34-5 3',5'-O-bis(triethylsilyl)-N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one 
• 50-89-5 thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 22003-31-2 N¹-(β-D-2'-deoxyribosyl)-5-methylpyrimidin-2-one 

Downstream Products

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

Relevant articles and documents

Mechanism of the alkali degradation of (6-4) photoproduct-containing DNA

The (6-4) photoproduct is one of the major damaged bases produced by ultraviolet light in DNA. This lesion is known to be alkali-labile, and strand breaks occur at its sites when UV-irradiated DNA is treated with hot alkali. We have analyzed the product obtained by the alkali treatment of a dinucleoside monophosphate containing the (6-4) photoproduct, by HPLC, NMR spectroscopy, and mass spectrometry. We previously found that the N3-C4 bond of the 5′ component was hydrolyzed by a mild alkali treatment, and the present study revealed that the following reaction was the hydrolysis of the glycosidic bond at the 3′ component. The sugar moiety of this component was lost, even when a 3′-flanking nucleotide was not present. Glycosidic bond hydrolysis was also observed for a dimer and a trimer containing 5-methyl-2-pyrimidinone, which was used as an analog of the 3′ component of the (6-4) photoproduct, and its mechanism was elucidated. Finally, the alkali treatment of a tetramer, d(GT(6-4)TC), yielded 2′-deoxycytidine 5′-monophosphate, while 2′-deoxyguanosine 3′-monophosphate was not detected. This result demonstrated the hydrolysis of the glycosidic bond at the 3′ component of the (6-4) photoproduct and the subsequent strand break by β-elimination. It was also shown that the glycosidic bond at the 3′ component of the Dewar valence isomer was more alkali-labile than that of the (6-4) photoproduct. The Royal Society of Chemistry 2012.