The 2-(N-Formyl-N-methyl)aminoethyl Group as a Potential Phosphate/Thiophosphate Protecting Group in Solid-Phase Oligodeoxyribonucleotide Synthesis
| Autor: | Marcin K. Chmielewski, Andrzej Grajkowski, Serge L. Beaucage, Lawrence R. Phillips, Andrzej Wilk |
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| Rok vydání: | 2001 |
| Předmět: |
Magnetic Resonance Spectroscopy
Biochemistry Thiophosphate Structure-Activity Relationship chemistry.chemical_compound Hydroxides Organic chemistry Physical and Theoretical Chemistry Protecting group Phosphoramidite Esterification Molecular Structure Phosphoric Diester Hydrolases Oligonucleotide Organic Chemistry Nuclear magnetic resonance spectroscopy Hydrogen-Ion Concentration Alkaline Phosphatase Chromatography Agarose Combinatorial chemistry Deoxyribonucleoside Ammonium hydroxide Monomer Oligodeoxyribonucleotides chemistry Ammonium Hydroxide Electrophoresis Polyacrylamide Gel Thymidine |
| Zdroj: | Organic Letters. 3:1287-1290 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol0156852 |
| Popis: | [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. |
| Databáze: | OpenAIRE |
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