A universal and recyclable solid support for oligonucleotide synthesis.
This unit provides a modified phosphoramidite method to synthesize oligodeoxyribonucleotides onto a universal and reusable hydroxyl solid support thanks to the use of deoxyribonucleoside tert-butyl and cyanoethyl phosphoramidites. The nucleoside tert-butyl phosphoramidite allows the introduction of an H-phosphonate diester linkage using the phosphoramidite method. After elongation, the H-phosphonate diester linker is cleaved by transesterification under mild basic conditions to yield an oligonucleotide with free 3'- and 5'-hydroxyls and the starting solid support. Thus, the solid support is easily recycled and used for a subsequent synthesis. In addition, a nucleoside tert-butyl phosphoramidite could be introduced inside the oligonucleotide chain during the elongation to yield a second H-phosphonate diester linkage. After elongation, the two H-phosphonate diester linkages are cleaved, producing two oligonucleotides with free 3'- and 5'-hydroxyls.
Morvan
François
F
Université Montpellier, Montpellier, France.
Meyer
Albert
A
Vasseur
Jean-Jacques
JJ
D000577:Amides / Q000737:chemistry; D002855:Chromatography, Thin Layer; D004951:Esterification; D009682:Magnetic Resonance Spectroscopy; D009841:Oligonucleotides / Q000138:chemical synthesis*; D010756:Phosphoric Acids / Q000737:chemistry
D000577:Amides; D009841:Oligonucleotides; D010756:Phosphoric Acids; C011067:phosphoramidic acid