1. The 2-(N-formyl-N-methyl)aminoethyl group as a potential phosphate/thiophosphate protecting group in solid-phase oligodeoxyribonucleotide synthesis.
- Author
-
Grajkowski A, Wilk A, Chmielewski MK, Phillips LR, and Beaucage SL
- Subjects
- Alkaline Phosphatase metabolism, Ammonium Hydroxide, Chromatography, Agarose, Electrophoresis, Polyacrylamide Gel, Esterification, Hydrogen-Ion Concentration, Hydroxides chemistry, Hydroxides toxicity, Magnetic Resonance Spectroscopy, Molecular Structure, Oligodeoxyribonucleotides chemistry, Oligodeoxyribonucleotides economics, Phosphoric Diester Hydrolases metabolism, Structure-Activity Relationship, Thymidine analogs & derivatives, Thymidine chemistry, Oligodeoxyribonucleotides chemical synthesis, Thymidine chemical synthesis
- Abstract
[reaction in text] The 2-(N-formyl-N-methyl)aminoethyl deoxyribonucleoside phosphoramidite 1 has been synthesized and used in the solid-phase synthesis of an octadecathymidylic acid as a cost-efficient monomer for potential application in the preparation of therapeutic oligonucleotides. The 2-(N-formyl-N-methyl)aminoethyl group can be cleaved from oligonucleotides according to a unique thermolytic cyclodeesterification process at pH 7.0. In addition to being cost-effective, the use of 1 simplifies oligonucleotide postsynthesis processing by eliminating the utilization of concentrated ammonium hydroxide in oligonucleotide deprotection.
- Published
- 2001
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