152873-34-2

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 148854-72-2 N-(3'-deoxythymidin-3'-yl)-N''-(5'-deoxythymidin-5'-yl)-N'-(p-methylphenylsulfonyl)guanidine 
• 148854-63-1 N-[1-{[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-amino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methyl-benzenesulfonamide 
• 25152-20-9 5'-amino-5'-deoxythymidine 
• 2651-15-2 N-[bis(methylthio)methylene]-p-toluenesulfonamide 

Relevant academic research and scientific papers

Synthesis, Enzymatic Stability and Base-pairing Properties of Oligothymidylates Containing Thymidine Dimers with Different N-Substituted Guanidine Linkages

Reaction of 5'-amino-5'deoxythymidine 1 with different S,S-dimethyl-N-substituted dithiocarbonimidates 2a-j afforded the N-substituted isothioureas 3a-j which, on further reaction with 3'-amino-3'-deoxythymidine 4 in the presence of AgNO3, led to thymidine dimers 5a-j with different N-substituted guanidine linkages.The dimer with a thiourea linkage (compound 9) was also prepared.Dimers 5a-h were incorporated at different positions in oligothymidylates by using phosphoramidite chemistry.Attempts to incorporate compounds 5i,j and 9 led to complex mixtures. 3'-Protected oligonucleotides showed somewhat higher stability to snake venom phosphodiesterase.Melting experiments revealed that the N-methylsulfonyl-substituted guanidine linkage best mimics the natural phosphodiester bridge.The fluorescence properties of oligonucleotides with dimer 5f were studied in view of its potential use as a non-radioactive label for DNA.