Synthesis and duplex-forming ability of oligonucleotides modified with 4′-C, 5′-C-methylene-bridged nucleic acid (4′, 5′-BNA). (15th September 2021)

• Record Type: Journal Article
• Authors: Yamaguchi, Takao; Yamamoto, Chika; Horiba, Masahiko; Aoyama, Hiroshi; Obika, Satoshi
• Is Part Of: Bioorganic & medicinal chemistry. Volume 46(2021)
• Publication Date: 2021-09-15
• Subjects: Artificial nucleic acid -- Therapeutic oligonucleotide -- Duplex-forming ability -- Nuclease resistance; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2021.116359
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: We describe herein the design and synthesis of 4′- C, 5′- C -methylene-bridged nucleic acid (4′, 5′-BNA), a novel artificial nucleic acid with the torsion angle γ in a non-canonical + ac range. The 4′, 5′-BNA phosphoramidite bearing a thymine nucleobase was synthesized from a commercially available thymidine analog in 11 steps and successfully incorporated into oligonucleotides. The resulting oligonucleotides were evaluated for their duplex-forming ability toward single-stranded DNA and RNA.