355819-79-3

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 355819-72-6 N⁶-benzoyl-9-(2-deoxy-3-O-(triisopropylsilyl)-β-D-erythrofuranosyl)-8-(hydroxymethyl)adenine 
• 355819-60-2 N⁶-benzoyl-9-[2'-deoxy-3'-O-(triisopropylsilyl)-β-D-glycero-tetrofuranosyl]adenine 

Downstream Products

• 355819-82-8 N⁶-benzoyl-9-[2'-deoxy-β-D-glycero-tetrofuranosyl]-8-[(4,4'-dimethoxytrityloxy)methyl]adenine 

Relevant academic research and scientific papers

Oligonucleotide Analogues with a Nucleobase-Including Backbone: Part 6. 2-Deoxy-D-erythrose-Derived Phosphoramidites: Synthesis and Incorporation into 14-Mer DNA Strands

Two modified DNA 14-mers have been prepared, containing either a 2-deoxy-D-erythrose-derived adenosine analogue carrying a C(8)-CH2O group (deA*), or a 2-deoxy-D-erythrose-derived uridine analogue, possessing a C(6)-CH2O groupp (deU*). These nucleosides are linked via a phosphinato group between O-C(3')(deA* and deU*) and O-C(5') of one neighbouring nucleotide, and between C(8)-CH2O (deA*), or C(6)-CH2O (deU*) and O-C(3') of the second neighbour. N6-Benzoyl-9-(β-D-eryhrofuranosyl)adenine (3) and 1-(β-D-erythrofuranosyl)uracil (4) were prepared from D-glucose, deoxygenated at C(2'), and converted into the required phosphoramidites 1 and 2. The modified tetradecamers 31 and 32 were prepared by solid-phase synthesis. Pairing studies show a decrease in the melting temperature of 7 to 8 degrees for the duplexes 31*30 and 32*29, as compared to the unmodified DNA duplex 29*30. A comparison with the pairing properties of tetradecamers similarly incorporating deoxyribose- instead of the deoxyerythrose-derived nucleotides evidences that the CH2OH substituent at C(4') has no significant effect on the pairing.