Improved synthesis of oligodeoxyribonucleotides

Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

“…For the oligonucleotide synthesis, separating the protecting-group removal from the support-cleavage step, commercially available glyceryl-CPG (CPG controlled-pore glass) was transformed into the DBU-stable LCAMA-CPG support (21) ((long-chainalkyl)methylamino linker) [9][10] by reaction first with 1,1'-carbonylbis[1H-diimidazole] (CDI ) and afterwards with N,N'-dimethylhexane-1,6-diamine ( Scheme 3).…”

Reactions at Oxygen Atoms

“…The solventswelling polymer supports previously employed have been replaced with controlled-pore glass supports (CPG) [35,38,229,230,231,232,233,234], and to the support, a chain with an appropriate spacer possessing a succinyl group at the outer end is attached; the succinyl group, in turn, is connected to the 3'-end of a nucleoside through the 2' or 3'-hydroxy group, the ester linkage being cleaved with conc. aqueous NH 3 at the end of the nucleotide synthesis.…”

Solid-phase synthesis of base-sensitive oligonucleotides

“…Figure 12). [54][55][56] The oligonucleotides are assembled on o-nitrophenylcarbonate derivatized resin (9) and then two-step deprotection procedure is carried out. The cyanoethyl groups of the phosphates are first selectively removed by a mixture of 40% triethylamine in pyridine and then the resins are subjected to a mixture of 0.5 M DBU in pyridine, which cleaves the p-nitrophenylethyl protections and concomitantly releases the target oligonucleotides.…”