852235-10-0

Upstream product

• 401906-98-7 1′,5′-anhydro-4′,6′-O-benzylidene-2′-deoxy-2′-(uracil-1-yl)-D-altro-hexitol 
• 92283-88-0 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol 
• 696-07-1 5-iodouracil 

Relevant academic research and scientific papers

Kinetic analysis of N-alkylaryl carboxamide hexitol nucleotides as substrates for evolved polymerases

Six 1,5-anhydrohexitol uridine triphosphates were synthesized with aromatic substitutions appended via a carboxamide linker to the 5-position of their bases. An improved method for obtaining such 5-substituted hexitol nucleosides and nucleotides is described. The incorporation profile of the nucleotide analogues into a DNA duplex overhang using recently evolved XNA polymerases is compared. Long, mixed HNA sequences featuring the base modifications are generated. The apparent binding affinity of four of the nucleotides to the enzyme, the rate of the chemical step and of product release, plus the specificity constant for the incorporation of these modified nucleotides into a DNA duplex overhang using the HNA polymerase T6G12 I521L are determined via pre-steady-state kinetics. HNA polymers displaying aromatic functional groups could have significant impact on the isolation of stable and high-affinity binders and catalysts, or on the design of nanomaterials.

Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis

D-Altritol nucleosides with an adenine and uracil base moiety were obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro- 4,6-O-benzylidene-D-allitol using the sodium salt of the above mentioned bases. The use of a 2-trimethylsilylethyl protecting group for the O6- function of the guanine base offers a useful compromise between stability and acceptable alkylation yields of the N9-position if the guanine base. The cytosine nucleoside was synthesized starting from the uracil congener. The 3'-hydroxyl function was protected with a benzoyl group.