20307-28-2

Upstream product

• 20816-58-4 adenosine 5'-phosphorimidazolide 
• 95314-00-4 adenosine 5'-phosphoromorpholidate sodium salt 
• 60031-83-6 adenosine 5'-phosphoroimidazolidate sodium salt 
• 95313-99-8 ImpA₂'p5'A sodium salt 
• 58-61-7 adenosine 

Downstream Products

• 2273-76-9 adenylyl(3'-5')phosphoadenine 

Relevant academic research and scientific papers

Lanthanide Ion as a Catalyst for Internucleotide Bond Formation

The lanthanide ion-catalyzed oligomerization of adenosine 5′-(l-imidazolylphosphate) was performed to yield short-chained oligoriboadenylates. The effect of lanthanide ions on the synthesis of oligoriboadenylates increased nearly in the order of the atomic number: None 3+?La3+?Ce3+?Pr 3+?Sm3+?Eu3+?Gd3+ 3+ ?Dy3+?Ho3+3+ 3+ 3+. The total yield of the oligoriboadenylates was 49% when Lu3+ was used as a catalyst. The linkage in the resulting oligoribadenylate was mainly 2′-5′.

Uranyl Ion as a Highly Effective Catalyst for Internucleotide Bond Formation

Uranyl ion catalyzes the polymerization of adenosine-5'-phosphorimidazolide very efficiently in aqueous solution.Up to 95percent of the imput adenosine-5'-phosphorimidazolide is converted to oligoadenilates from dimer to hexadecamer when 1mM of UO(2+) is used as a catalyst.The oligomeric products are predominantly 2'-5' linked.The chain length and the regioselectivity of the resulting oligoadenylates varies greatly with the concentration of the UO(2+) ion catalyst and the pH of the reaction medium.A high total yield of oligouridyllates up to dodecamer is also obtained by UO(2+) ion catalyst with high 2'-5' regioselectivity.The oligonucleotide formation is mediated by UO(2+)-nucleotide complex.

Expedient Chemical Synthesis of Sequence-Specific 2',5'-Oligonucleotides

A rapid chemical approach to the preparation of sequence-specific 2',5'-oligonucleotides and analogues of 2-5A is described.For instance, reaction of the 5'-phosphoromorpholidate of adenosine (MopA, 14) with the 5'-phosphoroimidazolidate of inosine (ImpI, 17), under conditions of lead ion catalysis, gave MopA2'p5'I (19a) in 21percent yield.Acid hydrolysis of 19a gave pA2'p5'I, which then was converted to the corresponding 5'-phosphoroimidazolidate Imp5'A2'p5'I (19c) through redox condensation with triphenylphosphine, imidazole, and 2,2-dipyridyl disulfide.Lead ion catalyzed condensation of 19c with Mop5'A (14) gave Mop5'A2'p5'A2'p5'I (30) in 17percent yield.By acid hydrolysis, 30 could be converted to the corresponding 5'-monophosphate, or, by reaction with pyrophosphate in DMF, to the corresponding 2-5A analogue, ppp5'A2'p5'A2'p5'I (5b).The following oligonucleotides were prepared by using similar methodology: ppp5'A2'p5'A2'p5'A (1b), ppp5'A2'p5'I2'p5'A (4b), ppp5'I2'p5'A2'p5'A (3b), and ppp5'A2'p5'A2'p5'(2'dA) (2b).