The solid-phase synthesis of 2'-5'-linked oligoriboadenylates containing 8-bromoadenine.
To increase the accessibility of 8-bromo-2',5'-oligoadenylates, we developed a synthesis of 2'-5'-linked oligoriboadenylates containing varying numbers of 8-bromoadenosine residues based on the use of a CPG-LCA solid support and the phosphoramidite approach. Although N6-benzoyl protection was satisfactory for incorporation of nonmodified adenine residues into 2',5'-oligonucleotides, the effective incorporation of 8-bromoadenine into such 2',5'-linked oligomers required use of a non acyl protecting group. Amidine protection of the purine exocyclic amino function proved compatible with all aspects of the phophoramidite approach and with the hydroxyl protection groups employed.
Lesiak
K B
KB
Section on Biomedical Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA.
Uznanski
B
B
Torrence
P F
PF
D000225:Adenine / Q000031:analogs & derivatives*; D000227:Adenine Nucleotides / Q000138:chemical synthesis*; D000469:Alkaline Phosphatase; D000577:Amides; D000578:Amidines; D002851:Chromatography, High Pressure Liquid; D005092:Exonucleases; D007202:Indicators and Reagents; D019906:Nuclear Magnetic Resonance, Biomolecular; D009843:Oligoribonucleotides / Q000138:chemical synthesis*; D043264:Phosphodiesterase I; D010756:Phosphoric Acids; D010727:Phosphoric Diester Hydrolases; D015719:Single-Strand Specific DNA and RNA Endonucleases
D000227:Adenine Nucleotides; D000577:Amides; D000578:Amidines; D007202:Indicators and Reagents; D009843:Oligoribonucleotides; D010756:Phosphoric Acids; C023505:2',5'-oligoadenylate; C027055:8-bromoadenine; C011067:phosphoramidic acid; D005092:Exonucleases; C086038:exonuclease, Aspergillus; D000469:Alkaline Phosphatase; D015719:Single-Strand Specific DNA and RNA Endonucleases; D010727:Phosphoric Diester Hydrolases; D043264:Phosphodiesterase I; D000225:Adenine