Synthesis of DNA Oligomers Possessing a Covalently Cross-Linked Watson–Crick Base Pair Model

✍ Scribed by Hong-Yu Li; Yao-Ling Qiu; Elisabeth Moyroud; Yoshito Kishi

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 128 KB
• Volume: 113
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3757(20010417)113:8<1519::aid-ange1519>3.0.co;2-#

✦ Synopsis

The concept of covalently cross-linked sections with molecular architecture similar to Watson ± Crick hydrogenbonded base pairs was introduced by Devadas and Leonard in the mid-1980s. [1] Since then, several types of covalently linked systems have been developed. However, these systems [2, 3] were generated from preformed double helices, as seen in the seminal work of Ferentz and Verdine. The Leonard system may offer unique opportunities to address questions regarding the chemistry of DNA and RNA, but this system has several drawbacks, including difficulty in attempted duplex formation and lack of conformational flexibility between the base pairs. [1] We have recognized the possibility that CH 2 -bridged base pair models may be uniquely suited to the chemical exploration of covalently cross-linked nucleosides/nucleotides. In addition to their increased chemical stability, these base pair models are expected to adopt only Watson ± Crick or reverse Watson ± Crick base pairings while maintaining conformational flexibility along the CH 2 bridge. We have focused on two specific types (types I and II) of base pair models (Scheme 1), with the anticipation that they might exhibit