Interestingly, N-acyl-protected purine nucleosides (particularly deoxyadenosine) are more prone to depurination than unprotected nucleosides. Among N-acyl-protected deoxyadenosines, protection at N6 with α-phenylcinnamoyl, naphthaloyl, 3-methoxy-4-phenoxybenzoyl, 9-fluorenylmethoxycarbonyl (FMOC), and tert-butylphenoxyacetyl …show more content…
Depurination is faster at terminal sites than at internal sites in an oligonucleotide chain (Suzuki et al., 1994). Interestingly, a solution of 15% dichloroacetic acid (DCA) in methylene chloride was ideal as a detritylating reagent that induced minimal depurination compared to the traditionally used 2% DCA/methylene …show more content…
(2009) prepared DNA probes S.55 from nucleosides S.16 incorporating thermolytic protetcing groups, N-arylcarbamoyl and N-(phenylsulphonyl)carbamoyl (psc), onto the amino groups of deoxycytidine, deoxyadenosine, and deoxyguanosine by reacting with corresponding isocynates (Figure X.X.X). Deprotection was carried out by heating under neutral conditions, enabling a new system of molecular switching by simply heating and reprotection with isocynates. Figure X.X.X shows deprotection mechanism under thermal conditions. A combination of thermolytic phosphate and amino protecting groups may lead to oligonucleotides that can be depeotected without any basic