Synthesis and evaluation of ( S )-5′- C -aminopropyl and ( S )-5′- C -aminopropyl-2′-arabinofluoro modified DNA oligomers for novel RNase H-dependent antisense oligonucleotides

Yujun Zhou; Ryohei Kajino; Seiichiro Ishii; Kenji Yamagishi; Yoshihito Ueno

doi:10.1039/d0ra08468a

January 1, 2020RSC AdvancesOpen Access

Synthesis and evaluation of ( S )-5′- C -aminopropyl and ( S )-5′- C -aminopropyl-2′-arabinofluoro modified DNA oligomers for novel RNase H-dependent antisense oligonucleotides

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Key Points

To design and synthesize novel (S)-5′-C-aminopropyl and (S)-5′-C-aminopropyl-2′-arabinofluoro modified thymidine analogs for incorporation into RNase H-dependent antisense oligonucleotides.
Designed and synthesized two novel nucleoside precursors: (S)-5′-C-aminopropyl-thymidine and (S)-5′-C-aminopropyl-2′-β-fluoro-thymidine.
Engineered chemical pathways to prepare modified building blocks suitable for DNA oligomer assembly.
Successfully achieved the chemical synthesis of (S)-5′-C-aminopropyl-thymidine.
Successfully produced the dual-modified analog (S)-5′-C-aminopropyl-2′-β-fluoro-thymidine for modified oligonucleotide development.

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Implication

Experimental study demonstrates the synthesis of novel aminopropyl-modified thymidine analogs, suggesting utility in RNase H-dependent antisense oligonucleotides.

Abstract

We designed and synthesized two novel thymidine analogs: ( S )-5′- C -aminopropyl-thymidine and ( S )-5′- C -aminopropyl-2′-β-fluoro-thymidine.

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Zhou et al. (2020) studied this question.

synapsesocial.com/papers/6a9e8c728f368e27c9231bb9 https://doi.org/10.1039/d0ra08468a

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Synthesis and evaluation of ( S )-5′- C -aminopropyl and ( S )-5′- C -aminopropyl-2′-arabinofluoro modified DNA oligomers for novel RNase H-dependent antisense oligonucleotides

Key Points

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Implication

Abstract

Discussion

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Synthesis and evaluation of ( S )-5′- C -aminopropyl and ( S )-5′- C -aminopropyl-2′-arabinofluoro modified DNA oligomers for novel RNase H-dependent antisense oligonucleotides

Key Points

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Abstract

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