805240-87-3

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 805240-78-2 (2R,3S,5R)-5-(2,5-Dimethyl-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol 
• 851518-06-4 (2R,5R)-5-(2,5-Dimethyl-phenyl)-2-hydroxymethyl-dihydro-furan-3-one 
• 173327-56-5 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose 
• 1122-42-5 2-iodo-p-xylene 

Downstream Products

• 1392279-62-7 C₄₆H₅₁N₂O₁₃P 
• 1392279-53-6 C₂₃H₃₁N₂O₁₀P 
• 1396637-20-9 C₆H₁₅N*C₄₆H₅₁N₂O₁₃P 
• 1392279-61-6 C₁₅H₂₀O₄ 
• 1392279-60-5 C₃₆H₃₈O₆ 

Relevant academic research and scientific papers

Indications of 5′ to 3′ Interbase Electron Transfer as the First Step of Pyrimidine Dimer Formation Probed by a Dinucleotide Analog

Pyrimidine dimers are the most common DNA lesions generated under UV radiation. To reveal the molecular mechanisms behind their formation, it is of significance to reveal the roles of each pyrimidine residue. We thus replaced the 5′-pyrimidine residue wit

Expanding the horizon of the thymine Isostere biochemistry: Unique cyclobutane dimers formed by photoreaction between a thymine and a toluene residue in the dinucleotide framework

Substituted toluenyl groups are considered as close isosteres of the thymine residue. They can be recognized by DNA polymerases as if they were thymine. These toluene derivatives are generally inert toward radical additions, including the [2+2] photocycloadditions, due to the stable structure of the aromatic ring and are usually used as solvents for radical reactions. Surprisingly, after incorporating toluene into the dinucleotide framework, we found that the UV excited thymine residue readily dimerizes with the toluenyl moiety through a [2+2] photoaddition reaction. Furthermore, the reaction site on the toluenyl moiety is not the C5=C6 bond, as commonly observed in cyclobutane pyrimidine dimers, but the C4=C5 or C3=C4 instead. Such a reaction pattern suggests that in the stacked structure, it is one of these bonds, not the C5=C6, that is close to the thymine C5=C6 bond. A similar structural feature is found in DNA duplex with a thymine replaced by a 2,4-difluorotoluene. Our results argue that although the substituted toluenyl moieties closely mimic the size and shape of the thymine residue, their more hydrophobic nature determines that they stack on DNA bases differently from the natural thymine residue and likely cause local conformational changes in duplex DNA.

Optimization of interstrand hydrophobic packing interactions within unnatural DNA base pairs

As part of an effort to expand the genetic alphabet, we have evaluated a large number of predominantly hydrophobic unnatural base pairs. We now report the synthesis and stability of unnatural base pairs formed between simple phenyl rings modified at diffe