Allyl group as a protecting group for internucleotide phosphate and thiophosphate linkages in oligonucleotide synthesis: facile oxidation and deprotection conditions.
[reaction: see text] The allyl group, which serves as a protecting group for an internucleotide bond for both phosphates and phosphorothioates, can be easily removed by good nucleophiles under weakly basic or neutral conditions. For a practical synthesis on solid support, camphorsulfonyloxaziridine was used as the oxidizing agent for synthesizing DNA, while the Beaucage reagent was used for preparing phosphorothioate oligomers. Both types of oligonucleotides were easily deprotected by concentrated ammonium hydroxide containing 2% mercaptoethanol.
Manoharan
M
M
Department of Medicinal Chemistry, Isis Pharmaceuticals, Carlsbad, California 92008, USA. mmanoharan@isisph.com
Lu
Y
Y
Casper
M D
MD
Just
G
G
D000114:Acetylene / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
D001572:Benzofurans; D006842:Hydrocarbons, Brominated; D010165:Palladium; D013890:Thiourea; C031387:carbon tetrabromide; D000114:Acetylene