Synthesis and photoreaction of 4 '-pivaloyl guanosides

Authors
Spormann, M Giese, B
Citation
M. Spormann et B. Giese, Synthesis and photoreaction of 4 '-pivaloyl guanosides, SYNTHESIS-S, (14), 2001, pp. 2156-2164
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
14
Year of publication
2001
Pages
2156 - 2164
Database
ISI
SICI code
0039-7881(200111):14<2156:SAPO4'>2.0.ZU;2-T
Abstract
The synthesis of a 4'-pivaloylated guanosine and its incorporation into oli gonucleotides is described. Photolysis of the modified nucleoside and DNA d ouble strand leads in nearly quantitative yield to enol ethers. The decisiv e step in this reaction is a very fast electron transfer from guanine to an enol ether radical cation.