Benzylidene Acetal Type Bridged Nucleic Acids: Changes in Properties Upon Cleavage of the Bridge Triggered by External Stimuli
✍ Scribed by Kunihiko Morihiro; Prof. Tetsuya Kodama; Prof. Satoshi Obika
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 425 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0947-6539
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Four classes of benzylidene acetal type bridged nucleic acids (BA‐BNAs) were designed with 2′,4′‐bridged structures that cleaved upon exposure to appropriate external stimuli. Cleavage of 6‐nitroveratrylidene and 2‐nitrobenzylidene acetal type BNA bridges occurred upon photoirradiation and subsequent treatment with thiol caused changes in secondary structure to afford 4′‐C‐hydroxymethyl RNA. Benzylidene and 4‐nitrobenzylidene acetal type BNA responded to acids and reducing agents, respectively, resulting in hydrolysis of the acetal‐bridged structure. Cleavage of the bridge removed sugar conformational restrictions and changed the duplex‐ and triplex‐forming properties of the BNA‐modified oligonucleotides. Moreover, oligonucleotides incorporating a single BA‐BNA modification had considerably improved stability toward 3′‐exonuclease, which was lost upon cleavage of the bridge. Thus, these new BNAs may be useful as therapeutic and detection tools by sensing various environments.