http://www.cnr.it/ontology/cnr/individuo/prodotto/ID50800
Adenosinyl Radical Cyclization. A Stereochemical Investigation (Articolo in rivista)
- Type
- Label
- Adenosinyl Radical Cyclization. A Stereochemical Investigation (Articolo in rivista) (literal)
- Anno
- 2006-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1021/jo060197z (literal)
- Alternative label
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Navacchia M. L.; Chatgilialoglu, C.; Montevecchi, P. C. (literal)
- Pagina inizio
- Pagina fine
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
- Rivista
- Note
- ISI Web of Science (WOS) (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
- Navacchia M. L.; Chatgilialoglu, C.: CNR, ISOF, I-40129 Bologna, Italy
Montevecchi, P. C.: Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy (literal)
- Titolo
- Adenosinyl Radical Cyclization. A Stereochemical Investigation (literal)
- Abstract
- A variety of substituted 2?-deoxyadenosin-5?-yl radicals 3 were generated under different reaction
conditions. Radicals 3 underwent intramolecular cyclization onto the C8-N7 double bond of the adenine
moiety leading to aminyl radicals (5?S,8R)-4 and (5?R,8R)-4 and, eventually, to the corresponding
cyclonucleosides 5 and 6. The effect of the solvent, the nature of the substituents, and the generation
method of radicals 3 on the stereoselectivity of the C5?-radical cyclization have been considered. The
observed increase of the (5?S)/(5?R) ratio by increasing the bulkiness of the R1 group is explained in
terms of steric repulsion between R1 and the purine moiety which favors the C5?-endo conformation,
whereas the effect of the water solvent in promoting the (5?R)-stereoselective cyclization is ascribed to
intermolecular hydrogen bonding stabilizing the C5?-exo confomation. (literal)
- Prodotto di
- Autore CNR
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