Effect of phosphate activating group on oligonucleotide formation on montmorillonite:  the regioselective formation of 3',5'-linked oligoadenylates.
The effects of amine structure on the montmorillonite-catalyzed oligomerization of the 5'-phosphoramidates of adenosine are investigated. 4-Aminopyridine derivatives yielded oligoadenylates as long as dodecamers with a regioselectivity for 3',5'-phosphodiester bond formation averaging 88%. Linear and cyclic oligomers are obtained and no A5'ppA-containing products are detected. Oligomers as long as the hexanucleotide are obtained using 2-aminobenzimidazole as the activating group. A predominance of pA2'pA is detected in the dimer fraction along with cyclic 3',5'-trimer; no A5'ppA-containing oligomers were detected. Little or no oligomer formation was observed when morpholine, piperidine, pyrazole, 1,2,4-triazole, and 2-pyridone are used as phosphate-activating groups. The effects of the structure of the phosphate activating group on the oligomer structure and chain lengths are discussed.
Prabahar
K J
KJ
Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York 12180-3590, USA.
Cole
T D
TD
Ferris
J P
JP
D015761:4-Aminopyridine / Q000031:analogs & derivatives*; D000241:Adenosine / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D001546:Bentonite / Q000737:chemistry*; D019418:Evolution, Chemical; D006868:Hydrolysis; D015636:Magnesium Chloride; D009841:Oligonucleotides / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D010758:Phosphorus / Q000737:chemistry*; D012965:Sodium Chloride
D000588:Amines; D009841:Oligonucleotides; D015636:Magnesium Chloride; D001546:Bentonite; D010758:Phosphorus; D012965:Sodium Chloride; D015761:4-Aminopyridine; D000241:Adenosine