Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis

✍ Scribed by S.L. Beaucage; M.H. Caruthers

• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 302 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90461-7

✦ Synopsis

The development of a new class of nucleoside phosphites is described. These compounds are stable to normal laboratory conditions, are activated by mild acid treatment, and are observed to react essentially quantitatively with protected nucleosides. A recent, key innovation in oligonucleotide synthesis was the introduction of the phosphite coupling approach by Letsinger and coworkers (l-3). This approach has been adapted to the syntheis of deoxyoligonucleotides (4-8), oligoribonucleotides (g-12), and nucleic acid analogs (13-15). Generally the approach involves the reaction of a suitably protected nucleoside, a bifunctional phosphitylating agent such as methoxydichlorophosphine, and a second protected nucleoside.