Acid‐Stable Nucleobase Protection for a Strongly Pairing Pyridone C‐Nucleoside Suitable for Solid‐Phase Synthesis of Oligonucleotides

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Oligonucleotides are indispensable resources in diagnostics, therapeutic programs and molecular biology. The lower foundation pairing strength of thymine with adenine complicates their use. Ethynylpyridone C -nucleoside are analogs of thymidine that pair far more strongly and with enhanced base selectivity, and sequences containing these analogs display enhanced goal affinity and selectivity, but their routine use is hampered by diminished yields of solid-stage syntheses with the identified making blocks. A partial decline of base guarding teams for the duration of the acidic deblocking step of chain extension cycles was identified as the lead to of reduce yields. Listed here we report the synthesis of an improved phosphoramidite building block that includes a pivaloyloxymethyl (POM) base guarding team. This developing block offers oligonucleotides that contains the strongly pairing ethynylmethylpyridone C -nucleoside in significant generate and purity by means of reliable stage synthesis.

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