Further optimization of detritylation in solid-phase oligodeoxyribonucleotide synthesis.
Various conditions for optimum detritylation (i.e., the removal of 5'-O-trityl protecting groups) during solid-phase synthesis of oligodeoxyribonucleotides were investigated. Di- and tri-chloroacetic acids of variable concentrations were used to study the removal of the 4,4'-dimethoxytrityl (DMTr) group. It was found that the DMTr group could be completely removed under much milder acidic conditions than what are currently used for automated solid-phase synthesis. The 2,7-dimethylpixyl (DMPx) is proposed as an alternative and more readily removable group for the protection of the 5'-OH functions both in solid- and solution-phase synthesis. The improved detritylation conditions are expected to minimize the waste and offer a protocol for incorporation of acid sensitive building-blocks in oligonucleotides.
Department of Chemistry, Brock University, St. Catharines, Ontario, Canada.
Kha
K
Tram
Yogesh S
YS
Sanghvi
Hongbin
H
Yan
D000143:Acids / Q000737:chemistry; D003999:Dichloroacetic Acid / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D014238:Trichloroacetic Acid / Q000737:chemistry; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
D000143:Acids; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D014320:Triphenylmethyl Compounds; D014238:Trichloroacetic Acid; D003999:Dichloroacetic Acid